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White steeples in opposition to crisp blue skies, superb autumn colours and fall foliage such as you wouldn’t consider, contemporary lobster rolls, REAL maple syrup – New England conjures all types of cozy associations! And a few not so cozy, like nice white sharks, witch-hunts, whaling, and rabid sports activities followers (don’t fear, they don’t assault until you’re carrying a Yankees hat). Whether or not you’re planning a fall getaway or a summer time trip, the shoreline and mountains of New England make for one really unforgettable highway journey!
My household hails from New England way back to the Mayflower, and for the primary 3 years of my life, I used to be a full-fledged Bostonian – accent and all. I spent fairly a little bit of time visiting Massachusetts rising up: staying with household in Cape Cod, visiting my sister in school in Boston (Wellesley), briefly attending faculty in Western Massachusetts (Mount Holyoke), and interning for one sunny summer time in Newburyport. However I’ve but to finish a full-fledged New England highway journey… which is why I tapped journey author and Massachusetts native Anna Laird Barto to create the right itinerary!
This New England highway journey itinerary visits Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island and captures as a lot of New England’s allure, magnificence, historical past and quirkiness as potential in ten days – with loads of stops for witches, ghosts, and lobsters alongside the way in which. Take it away, Anna!
Psst: Planning on exploring extra of the East Coast? Check out a few of our different posts!
New England Street Journey FAQs
As a result of the entire of New England is relatively small – in regards to the dimension of Arizona – outsiders typically underestimate the variety inside the area. Once I inform individuals out west I’m from Massachusetts, they instantly assume I’m from Boston.
Truly, my hometown of Amherst is nearer to Vermont. And nobody on this a part of the state feels like JFK or an Irish mobster from a Scorsese movie. I wish to suppose that we’re higher drivers too.
Aside from the place you’ll discover the worst drivers in New England (ahem: Boston), there are just a few extra stuff you’ll must know earlier than taking your New England highway journey.
The place ought to I fly out and in of?
This itinerary begins and finishes in Boston. Boston Logan is without doubt one of the busiest airports within the nation, with continuous service to and from a whole bunch of locations worldwide. It’s additionally only a 10-20 minute drive from downtown, relying, as at all times, on the visitors!
The place ought to I hire a automotive?
All the most important car rental businesses function out of Logan. However be forewarned that parking areas are probably the most coveted actual property within the metropolis. If you happen to keep anyplace close to downtown, you’ll pay to park, sometimes between $25-$39 per day.
An alternative choice is to take a Lyft to your lodge and decide up your automotive the following morning, both at Logan or a downtown location. You received’t want or desire a automotive to get round downtown.
- Journey Tip: Booked your flight and rental car but? We suggest utilizing Kayak to price-compare offers and dates to save cash… so you may spend extra on meals throughout your journey (#letsbehonest).
What’s one of the best time of the 12 months to take a New England Street Journey?
Go within the fall should you can, and put together to be spoiled for fall anyplace else for the remainder of your life. It’s not solely in regards to the leaves, which morph into each possible tone of gold, orange, purple, and brown, however the crisp, clear air and the solar burning by way of the morning mist.
The farther north you go, the sooner the leaves change coloration, though the precise timing varies as a result of issues like common annual rainfall and temperature. Typically, peak colours seem in Maine and northern New England across the finish of September, whereas Connecticut could not see peak colours till nearly Halloween.
If you happen to can’t swing a fall journey, summer time is an in depth second. The climate may be downright sultry, particularly in southern New England, however the ocean, seashores, and spring-fed swimming holes are chilly and refreshing! Plus, summer time is the best time of 12 months for a scrumptious lobster roll!
Issues To Know Earlier than Taking a New England Street Journey?
- In New England we’ve got “highways” not “freeways.” We often check with them by quantity: 495, 91, and so forth., apart from Route 90, which is solely “the Pike.” This itinerary avoids the Pike as a result of it’s stuffed with vans and potholes.
- Look ahead to deer, moose… and wild turkeys! Flocks of untamed turkeys are frequent even within the suburbs. Once they resolve to cross the highway, spare your horn: no energy on earth could make them hurry up.
- Drive instances can differ dramatically relying on visitors, particularly round Boston. We did warn you in regards to the drivers in Boston, proper?
- Don’t be fooled by our gruff exterior. New Englanders may not appear pleasant, however we’re secretly dying to let you know all about this place we name house. Simply don’t get my dad began on the geology of Cape Cod’s Kettle Lakes!
What’s the historical past of New England?
Everyone knows the model that we realized in class: in 1600-something, a bunch of English Puritans looking for spiritual freedom (and fewer taxes) sailed throughout the ocean within the Mayflower (together with Lia’s problematic ancestor, Miles Standish) and arrived at Plymouth Rock, near demise and with completely no clue what they have been doing. Because of the generosity of the Indigenous peoples, they thrived sufficient to subsequently take over all the continent. The remainder – witch hunts and revolutions and all, see Hamilton and The Crucible for particulars – is historical past.
However what in regards to the historical past of New England BEFORE the arrival of the Mayflower? 1000’s of years earlier than the US (a lot much less the Purple Sox) declared itself a nation, this northeastern tip of Turtle Island was cared for by the Nipmuc, Massachusetts, Mohegan, Mohican, Narraganset, Nauset, Niantic Schaghticoke, Pocumtuc, Pequot and Wampanoag nations, and the affiliated tribes of the Wabanaki Confederacy.
At this time, New England’s Native peoples (sure, they’re nonetheless right here!) determine as 16 distinct Nations and Tribes. They proceed to carry their floor, regardless of ongoing challenges to their sovereignty, similar to in 2020, when the US Division of Inside tried to revoke the belief standing of the Mashpee Wampanoag homelands.
The Final New England Street Journey Itinerary
You’ll be driving rather a lot, however this itinerary makes a degree of taking the scenic route, with frequent alternatives to cease in quaint small cities. Selecting which of them to function is nearly like selecting between my kids, so when you have additional time, keep an additional night time anyplace alongside the way in which!
With out additional ado let’s get began in your New England highway journey!
Day 1: a Correct Day in Boston, Massachusets
- At this time you’ll get probably the most correct Boston expertise potential in a single day.
- Drive Time: None. Happily, Boston is one in every of America’s “Most Walkable” cities, as a result of it’s one of many worst locations to drive, a lot much less park. Apart from, it wouldn’t be a Correct Boston expertise with out taking mass transit, higher often called the “T.”
Ahhh, Beantown. Welcome to Bahstan: a metropolis outlined by its wealthy historical past and sports activities tradition, stuffed with homey, Cheers-esque bars and a thriving theater scene, with harbor views round each nook and a bustling metropolis middle that by some means feels each previous and new on the identical time.
New England’s largest metropolis occupies the hilly peninsula often called Shawmut by its authentic stewards, the Massachusetts, Wampanoag and Nipmuc individuals.
There isn’t a approach to see all the things in Boston sooner or later, however with some good planning, you may see rather a lot. My private choice – extra of a bias – is for the Italian North End and Charlestown, the place I ran a neighborhood program for a few years.
It doesn’t matter what time your flight will get in, you may get a full breakfast, and/or a cocktail, on the Friendly Toast within the Again Bay (name a Lyft or take the Orange Line Train to Again Bay Station).
A great way to see a number of sights in a brief period of time, particularly should you’re drained from an extended flight, is to squeeze all of it in on a Duck Tour. The notorious Duck boat – a World Battle II-style amphibious car – is a Boston icon in its personal proper! The 80-minute tour takes you previous landmarks like Boston Common, Faneuil Hall, and Quincy Market, earlier than plunging into the Charles River for a duck’s-eye view of town skyline.
For lunch – or dinner, relying on when your flight will get in – head to the previous Italian North End. Locals argue to the demise about whether or not the pizza is best at Regina’s or Umberto’s, or if Modern Pastry or Mike’s has higher cannolis. My favourite is whichever has the shortest line!
Observe the Freedom Trail (marked by a redbrick line) by way of the charming cobblestone alleys of the North Finish and throughout the bridge to Charlestown. Take within the view from the Bunker Hill Monument (truly on Breed’s Hill) earlier than hitting Paul Revere’s favourite hangout, The Warren Tavern, for dinner and/or drinks.
- Tip: Watch Ben Affleck’s The Town for an action-packed however surprisingly advanced introduction to Boston’s oldest neighborhood – plus a cameo by the proprietor of my favourite laundromat!
The place to Keep: The Harborside Inn affords one of the best worth for one of the best location, a brief stroll from the harbor, duck tour, Freedom Path, Quincy Market, and a number of other T stops. Or, should you’re feeling adventurous, you may keep immediately IN the harbor on a houseboat! (Be happy to pour a little bit tea over the facet to actually get within the spirit of issues, too.)
Day 1 Abstract


Day 2: Boston to Portland, Maine (with a spooky Salem stopover)
- At this time you’ll head up the seacoast to Portland, Maine, stopping on the notorious city of Salem.
- Drive Time: 2-3 Hours
Earlier than hitting the highway, seize breakfast and collect provisions on the Boston Public Market, an indoor market the place you’ll discover all the things from maple bacon glazed donuts to Kelp Smoothies.
Now it’s on to Salem, about 40 minutes north by way of the Essex Coastal Scenic Byway (Route 127) which takes you thru the elegant seaside communities of Swampscott and Marblehead. In contrast to Boston, Salem has ample public parking, and all sights are inside simple strolling distance.
If it weren’t for the 1672 Salem Witch Trials, Salem could be simply one other, albeit very beautiful, North Shore port city. As a substitute, this small city is the worldwide epicenter of all issues occult.
Within the twenty first century Salem, it’s nonetheless laborious to separate the historical past from the hype. My recommendation is to embrace the insanity, which through the month of October is just about 24/7.
For a glance behind the hype, join Kenneth Glover’s Morning Stroll Historical Tour. Kenneth supplies an outline of the Witch Trails AND Salem’s Native American and maritime historical past as you stroll by way of Salem’s slender streets previous Seventeenth-century landmarks just like the Salem Witch House and Hamilton Hall.
After lunch on the Lobster Shanty – well-known for its “heat beer, awful meals, surly waitresses, impolite bartenders, and cranky cooks” – immerse your self in witch kitsch earlier than hitting the highway for the 1-2 hour drive to Portland. Get a psychic studying, fill up on spell-casting provides, or go to the Salem Wax Museum.
You probably have an additional day in Salem:
Bounce again on Route 127 till your bladder provides you an excuse to cease in Manchester-by-the-sea, Gloucester, Rockport or charming Newburyport. (Aspect notice from Lia: Newburyport is beautiful! I spent a cheerful summer time right here working at an internship on the harbor. Extremely suggest a pit cease!)
Say howdy to New Hampshire for a scorching second (don’t fear, you’ll be again) earlier than arriving in Portland, Maine, in what was as soon as the center of the Wabanaki Confederacy. The drive from Salem to Portland is about an hour and forty minutes.
Portland, Maine, is the older, colder – wiser? – cousin of Portland, Oregon. Like their west coast counterparts, Portland Mainers are enthusiastic about artwork, the outside, and their native microbrews, which you’ll have the chance to pattern.
However first, cease in on the International Cryptozoology Museum, as a result of what higher approach to get into the temper for the Maine Woods than studying about huge furry cryptids? Notable exhibitions embrace Bigfoot hairs and Abominable Snowman scat. You may as well decide up a Santa Yeti Christmas decoration for mother on the CryptoStore!
By now, you most likely want a drink, so it’s on to Allagash, Austin Street, and/or one other of Portland’s native breweries for a palate-cleansing flight of beer or cider, earlier than chowing down on some nouveau, New England meals at Central Provisions.
The place to Keep: You most likely received’t be spending a lot time on the lodge, however the Inn at St John affords clear, quaint lodging at inexpensive charges. Or select one of many fancier West Finish B&Bs like Chadwick’s.
Day 2 Abstract


Day 3: Scenic Drive by way of Maine to Acadia
- Head down east alongside coastal Route 1 to Bar Harbor, stopping for lunch at McLoons Lobster Shack.
- Drive Time: 2.5-3 hours
Even should you ate breakfast at your B&B, it is best to nonetheless cease at Tandem Coffee Roasters in your manner out of city. You’ll be able to’t replenish the automotive at this transformed ‘60s fuel station, however you may refuel on single-origin espresso, cinnamon buns and yummy scones!
Maine has about 3,478 miles of coastline, greater than California (simply extra squiggly), and right now you’re going to see a number of it: waves crashing on rocky seashores, sailboat-studded bays, Hallmark villages and scenic lighthouses.
Take a detour down Route 130 to the Pemaquid Point Lighthouse, about 40 minutes round-trip, perched dramatically atop a layer cake of metamorphosed rock.
We promised lobster, and it’s time to money in within the state the place it’s probably the most contemporary and most cheap! Cease for lunch at an genuine Maine lobster shack, just like the (deservedly) well-known McCloon’s Lobster Shack in South Thomaston and Claws in Rockland, about an hour-and-a-half from Portland. These quirky roadside stands usually shut for the season across the finish of September – test the web sites for actual dates. However fall road-trippers are in luck: an exception is Hazel’s Takeout in Rockland, which stays open till November.
Whilst you’re in Rockland, take a look at the Archipelago, a retailer that helps artists and makers from Maine’s small coastal and island communities.
Proceed on Route 1 by way of historic downtown Camden. Cease simply up the highway at Camden Hills State Park. Drive or stroll to the highest of Mount Battie for views of Camden Penobscot Bay and islands; views that impressed the poem “Renascence,” by Edna St. Vincent Millay.
From right here it’s about an hour-and-forty-five minute drive to the beautiful Acadia National Park, the jewel of Maine and arguably one of the best Nationwide Park on the Japanese seaboard! You’ll be exploring tomorrow, so test into your lodge and head to dinner.
For dinner, we suggest Side Street Cafe, a much less touristy spot by Bar Harbor requirements. It serves quite a lot of all-American fare however it’s greatest identified for lobster rolls and blueberry pies, to not point out blueberry margaritas and blueberry ale.
The place to Keep: The closest city to the park is Bar Harbor. The charming Moseley Cottage Inn is the sweetest, most charming little quintessential New England B&B, and the Bar Harbor Inn & Spa is a extra upscale boutique lodge.
Inns right here may be expensive, however there are some inexpensive, no-frills choices. Many guests to Acadia select to camp as an alternative. We all know it’s laborious to pack tenting gear in your suitcase, so we discovered one thing even higher – glamping! Reserve a safari-style A-frame tent in Lamoine, about thirty minutes north of the park. This private bay retreat comes with a photo voltaic bathe, moveable camp rest room and propane heater for cool fall nights.
Day 3 Abstract:
Day 4: Bar Harbor and Acadia Nationwide Park, Maine
- At this time you’ll expertise one in every of America’s most luxurious nationwide parks.
- Drive time: 0-3 hours, largely inside Acadia Nationwide Park
Route 1 was solely a scenic warm-up! To expertise Acadia National Park is to step again in geologic time – mountains cut up by receding glaciers, waves crashing in echo chambers of volcanic rock, spruce-covered islets and countless deciduous forest that bursts into coloration every fall.
That is the sacred panorama of the Wabanaki individuals, who nonetheless come right here to reap sweetgrass and go climbing!
The easiest way to understand Acadia is to hike the trails. You probably have an additional day or two, it is a nice approach to spend them. Nevertheless, the park additionally has shorter trails that match into any itinerary, together with this one.
Head out early and seize breakfast (to-go or at one in every of their picnic tables) from Hull’s Cove General Store. You may as well decide up snacks and picnic provides; they’ve a full-service deli, baked items, pizza, and comfort retailer gadgets.
One possibility is to depart your automotive on the Hulls Cove Visitor’s Center and take the Island Explorer shuttle bus, which picks up and drops off at standard locations inside the park.
You’ll be able to full the Beehive Loop, Ocean Path, or South Bubble Trail by lunchtime. Eat the picnic you packed from the overall retailer, or head to the Jordan Pond House for popovers and tea.
After lunch, hold climbing, or tour park highlights. Journey the shuttle or take a self-guided driving tour of the park (roughly three hours) culminating with mind-blowing views from Mount Cadillac. If potential, time your journey so that you could watch the sunset from the summit.
For dinner head again to Bar Harbor for old style pub meals and brews on the Thirsty Whale Tavern, or, particularly should you’re staying in Lamoine, the Acadia Lobster and BBQ in Trenton.
Day 4 Abstract:
Day 5: Maine to New Hampshire, the Northeast Kingdom
- At this time’s drive takes you west alongside the Androscoggin River by way of the city of Bethel and up into the beautiful White Mountains of New Hampshire!
- Drive time: 4.5 hours
Begin with a hearty Great Maine Breakfast earlier than heading north and west to Bethel by way of Route 2, a couple of four-hour drive. Take a brief detour to see the Sunday River Covered Bridge in Newry. If the weathered truss bridge seems acquainted, that’s as a result of it’s; the Sunday River Bridge is also called the “Artist’s Bridge,” as a result of it’s mentioned to be probably the most painted and photographed bridge on the earth.
Eat lunch and fill up on snacks at Good Food Bethel, which is – no kidding – a espresso store, well being meals retailer, delicatessen, liquor retailer, AND BBQ joint in a single.
After lunch, take a look at the Maine Mineral & Gem Museum, house of the biggest moon rock on earth.
Take the remainder of the afternoon to go raspberry selecting (should you’re there in July) or apple selecting (in September) at Gibson’s Apple Orchard. The orchard retailer is open till round Thanksgiving, promoting do-it-yourself cider, native honey and maple syrup, so it’s price a cease on a fall day!
From right here it’s solely a 30-minute drive to Gorham, New Hampshire, your base for exploring the White Mountains. You’ll discover the backbone of the Carter-Moriah range rising to the southwest.
As you cross over the New Hampshire border, you’ll see a proliferation of billboards promoting issues like alcohol and cigarettes. New Hampshire is the “Dwell Free or Die” state, and naturally demise is preferable to paying gross sales tax… or carrying a helmet whereas using a motorbike.
For dinner in Gorham attempt The Notch Grille at The Glen House Hotel, the place the one factor higher than the meals is the views. Ground to ceiling home windows face the Presidential Vary, evergreen slopes giving approach to granite escarpments blanketed with snow for many of the 12 months.
Within the Algonquin language, these mountains are often called Wobanadenock, “the place of the excessive white or crystal/mica mountains.” The tallest of those peaks, typically shrouded in clouds, is Mount Washington, house of among the highest wind speeds on earth – that’s the place you’re going tomorrow!
The place to Keep: Keep at The Glen House: If these firepits on the deck with sweeping mountain views don’t do it for you, maybe the complimentary breakfast and cookies will! Or lean into the log cabins/alpine chalet vibe and keep at this stunning vacation rental, with unimaginable views, a super-modern kitchen, and an enormous stone hearth!
Day 5 Abstract:
Day 6: New Hampshire to Vermont (the White Mountains to the Inexperienced Mountains)
- At this time you’ll climb Mount Washington and traverse the Kancamagus Scenic Byway in your approach to the Inexperienced Mountains of Vermont.
- Drive Time: 2.5 hours
Eat breakfast on the homey White Mountain Cafe and Bookstore, the place it’s also possible to decide up path maps and native curiosity books.
By now you will have observed the bumper stickers: “This Automobile Climbed Mount Washington.” Until you might have a complete day, and are a seasoned mountaineer, one of the simplest ways to climb New England’s highest peak is by way of the auto highway! (After which you may decide up a bumper sticker, too!)
The slender, two-lane autoroad, accomplished in 1864, ascends 6,145 ft by way of a sequence of steep switchbacks. There are NO guardrails. If that is an excessive amount of for you, no disgrace. Join the guided tour, and let another person do the driving.
The round-trip lasts about three hours, taking you from the leafy hardwood forest by way of boreal groves of evergreens and birch, gnarled conifers and blueberries, earlier than rising onto windswept alpine tundra. Many of the 12 months, the summit is snowy, with thrilling views of close by peaks poking up by way of the clouds.
At 6,145 ft, Mount Washington could seem puny in comparison with peaks out west, however don’t be fooled — as a result of its location on the intersection of storm tracks from the south and west, the summit experiences among the most excessive climate circumstances on earth. Winds as excessive as 230 mph have been recorded on the Mount Washington Observatory. You may be reassured that the auto highway shall be closed if circumstances even remotely method that.
If you wish to forgo being in a automotive altogether, you may take the long-lasting Mount Washington Cog Railway to the highest, which was the primary mountain-climbing cog railway ever constructed. Opening in 1868, the biodiesel and steam train takes about three hours round-trip. On the summit, you may pick a memento on the Sherman Adams Summit Building and go to the Tip Top House, a former lodge courting again to the nineteenth century that was changed into a historic website. It’s price noting that from Oct. 18 to 31, there’s a special train that takes you to the north and east of the mountain.
After your mountain tour, get pleasure from some elegant consolation meals on the four-season porch on the Wildcat Inn and Tavern in Jackson. After lunch, it’s time to hit “Kanc,” or Kancamagus Scenic Byway, which cuts by way of the center of the White Mountain Nationwide Forest. It’s solely about an hour and forty-minute drive from Jackson to Littleton, however depart extra time, as a result of there’ll be a number of alternatives to cease and ooh and ahh over the foliage, take a brief hike, or test some extra covered bridges off your listing.
Final cease in New Hampshire is Littleton, a captivating mill city that usually flies underneath the vacationer radar. Seize a beverage or snack on the Inkwell Coffee & Tea House or just stretch your legs alongside the half-mile Riverwalk.
- Psst: A number of of those stops – and a complete bunch extra – are lined in our guide to fall in New Hampshire! New Hampshire is sufficiently small to base your self in a single spot and take scenic drives to see the remainder of the state, so should you really feel like spending just a few additional days within the White Mountains, head over to that publish for extra journey suggestions.
It’s time to depart beautiful New Hampshire and dive into charming, lovely Vermont. From Littleton, observe Route 2 east to the “NEK” – North East Kingdom of Vermont – land of mountains, lakes, small farms, and ICE CREAM.
That’s proper: you may’t go to Vermont with out making a pilgrimage to the ice-cream shrine of Ben & Jerry’s in Waterbury (about an hour and a half drive from Littleton). Take a Factory Tour and go to the Scoop Store, serving classics like “Cherry Garcia,” in addition to blasphemous new “Netflix Authentic Flavors” like “Netflix and Chilled.”
Drive twenty minutes north to the village of Stowe, the place you’ll be staying tonight! This ski resort vacation spot hangs onto its small-town allure, with a energetic foremost avenue anchored by an iconic steepled church and native companies like Laughing Moon Chocolates and Shaw’s General Store.
For dinner, head to Stowe’s hippest pizza place, The Deep End, the place you order a drink from the refurbished airstream bar!
The place to Keep: Ebook a room on the Timberholm Inn, a comfortable mattress and breakfast overlooking the mountains.
Day 5 Abstract:
Day 7: The Two Faces of the Berkshires
- At this time, you’ll take the again roads to the Berkshires by way of the Inexperienced Mountain Nationwide Forest, stopping at MASS MoCa in North Adams, Massachusetts.
- Drive Time: 3.5 hours
Begin with breakfast at The Skinny Pancake, a Vermont chain that’s truly higher identified for its candy and savory crepes that includes elements like maple pulled pork, native cranberry compote, and hazelnut unfold.
From Stowe, take Route 7 south. You’ll keep on 7 for the following three hours. For many of the manner, 7 is a rural, two-lane freeway, winding by way of quintessential Vermont countryside: purple barns, dairy cattle, and rolling inexperienced mountains. You already know, typical jaw-dropping New England surroundings.
Arriving in North Adams, simply over the Massachusetts border, you’ll see one other facet of New England: a former industrial city that’s reinventing itself as an arts middle.
Eat lunch at Lickety Split, a family-run eatery and ice cream parlor on the Massachusetts Museum of Contemporary Art (MASS MoCA). The menu is easy – soups, salads, quiches and sandwiches – however created from the freshest locally-sourced elements. The ice cream can also be made in-house, utilizing flavoring strategies pioneered by Ben & Jerry’s rival Steve Herrell.
The museum has reworked an deserted brick manufacturing unit advanced right into a multi-media artwork house. The football-field-sized Constructing 5 homes epic installations, like Glen Kaino’s “Within the Gentle of Shadows,” wherein 1000’s of suspended steel shards mission otherworldly patterns of sunshine throughout the huge warehouse house.
Now it’s on to the Berkshires. Simply an hour’s drive south lies the playground of wealthy Manhattanites. You’ll be able to hardly blame them: southwestern Massachusetts is each culturally wealthy and classically scenic.
Nowhere is that this higher epitomized than at The Mount, the sprawling romantic property of creator Edith Wharton. Home excursions finish at 5pm, however the grounds of the 1902 mansion are open free from daybreak till nightfall.
Wander freely across the in depth gardens designed by Wharton herself, impressed by her travels to France and Italy. If you happen to’re left wanting extra, return after dinner for a ghost tour of the property, which has been featured in a number of episodes of Ghost Hunters.
Keep on the historic Church Street Inn in downtown Lennox, steps from fashionable eating places like Alta, a Mediterranean-style cafe and wine bar, the place you may dine alfresco and watch the attractive individuals – and drained vacationers – move.
Day 7 Abstract:
Day 8: Connecticut, Rhode Island, & Cape Cod
- At this time you’ll move by way of three totally different states in your approach to Cape Cod, stopping for lunch and surroundings on the Connecticut coast and Newport, Rhode Island.
- Drive Time: 5.5 hour
Eat breakfast on the porch at Ophelia’s, the Church Street Inn’s personal restaurant, the place the menu ranges from huevos rancheros to lemon ricotta pancakes with blueberry compote and – after all – native maple syrup. (If you happen to will need to have Aunt Jemimah’s, conceal it in your purse).
At this time you’ll be protecting a number of floor, however it’s lovely floor. Ignore all these indicators for the Mass Pike and keep on Route 7 by way of Stockbridge and Nice Barrington. You’ll keep on Route 7 for the following hour, earlier than chopping by way of Litchfield Hill to Torrington.
From there, it’s about one other hour and forty-five minutes to the coast. No, this isn’t probably the most direct route, however belief me, it’s a lot prettier than the 91 hall and effectively well worth the detour.
If you happen to’re a Julia Roberts fan, cease for lunch at Mystic Pizza, which is an actual place with respectable pizza and plenty of film merch. Or, go for Kamp Dog in New London, “New England’s Best Wienery.”
Now that you just’ve dined in model, you’re able to enter Newport excessive society. Set your personal tempo on this 1-2 hour Self-guided Driving Tour, which takes you previous the “summer time cottages” – AKA gilded age mansions – of the wealthy and well-known.
From right here, it’s a little bit over an hour (if the visitors Gods are smiling) to your penultimate vacation spot: Cape Cod!
For the following two nights, hire a beach cottage in East Sandwich, full sweeping ocean views, hammocks, and your very personal personal seaside entry. Take a sundown stroll alongside the white sand seaside earlier than having fun with dockside boat-to-table delicacies at Fisherman’s View.
Day 8 Abstract:
Day 9: Cape Cod Magic
- Relaxation and play on the decrease Cape.
- Drive Time: 0-1 hour
You’ve been on the highway for over every week. You’ve earned a relaxation, and what higher place for it than Cape Cod, the flexed arm of Massachusetts.
Sandwich could also be simply over the bridge from the “mainland,” however it’s quintessentially Cape Cod, with its sandy seashores, salt marshes, lighthouses, and cottages with weathered gray shingles.
Sandwich is Cape Cod’s oldest English settlement courting again to 1639, and the land adjoining stays sovereign to the Mashpee Wampanoag, the primary individuals to come across the Pilgrims.
Sleep in as late as you need, then seize breakfast at Cafe Riverview, a preferred spot staffed by college students from the native highschool.
After breakfast, spend the morning hanging out out on the seaside. Sandwich is situated on the Bay facet of Cape Cod, so the waves are calm. The seashores are sheltered by sand dunes lined in lengthy waving grasses, which fade to pale straw in autumn.
Stroll the Sandwich Boardwalk whilst you can. The 100+ 12 months plank bridge, which extends 1300 ft throughout the salt marsh to Cape Cod Bay, is ready to be demolished soon and changed with one thing uglier and extra structurally sound.
Eat lunch at Cafe Chew, “Sandwich’s Sandwichery.” I don’t know what the Earl of Sandwich (alleged inventor of the sandwich) would make of their “Oatsy-Groatsy” sandwich with cucumber, child spinach, tomato, feta cheese, pureed purple pepper, caramelized onion, and hummus in a complete wheat wrap, however it sounds good to me.
Stroll the Sandwich Historic District for a final glimpse of the sixteenth century earlier than returning to modernity. Tour the interiors of Cape Cod’s oldest properties, the Hoxie House and the Wing Fort House. They’re at the moment closed as a result of pandemic, however you may nonetheless admire the post-medieval timber body development, with uneven “saltbox” formed roofs from the surface.
The irresistibly photogenic Dexter Grist Mill, inbuilt 1654, overlooks Decrease Shawme Pond, which is shaded by weeping willow bushes and residential to households of geese and swans. The mill nonetheless operates, and from Might by way of September you should buy a bag of its fresh-ground cornmeal.
Eventually, it’s time to strap in your bib for a remaining feast of fried seafood and butter-drenched lobster at Mattakeese Wharf.
Day 9 Abstract:


Day 10: Returning Residence
- Full the circle (blob?) again to Boston. You probably have time, cease by within the well-known city of Plymouth. Drop off your rental automotive and catch your flight house!
- Drive Time: 1.5-2 hours
Although it’s your final day, it doesn’t imply that you would be able to’t squeeze a bit extra New England historical past in (in case your flight time permits, that’s!).
Earlier than you permit Cape Cod, eat a traditional Ameican breakfast at 6a Cafe then hop on the highway in direction of Plymouth.
Plymouth, Massachusetts, after all, is the place the Mayflower Pilgrims landed in 1620 and the “new world” was born (not less than to British people—America was already inhabited). For good or ailing, Plymouth was the primary colony established by the pilgrims, and it holds one of many high spots in American lore.
A pure first cease is the Plymouth Rock, which can or is probably not the “actual rock”, however was recognized because the spot of the Mayflower touchdown in 1741, 121 years after the actual fact.
Whilst you’re within the space, you may take a look at the reproduction ship the “Mayflower II“, in addition to Historic Patuxet, the place Native Peoples lived for 12,000 years earlier than being entirely wiped out by an epidemic. You may as well go to the Plymouth Colony, to see how the Pilgrims labored and lived. The whole museum advanced is immersive with actors in interval costumes, and you may simply spend the entire day studying in regards to the individuals who as soon as lived within the space.
- Aspect Observe: On the Plymouth Colony you’ll get an opportunity to satisfy Lia’s problematic ancestor, Miles Standish. Captain Miles Standish was first mate of the Mayflower and the navy chief of the Pilgrams, and was additionally the one individual on the Mayflower to be overtly non-religious – he by no means joined the church. Why is he problematic, you ask? Effectively, as navy chief of the Pilgrims, he kind of unintentionally ended the peace between the Pilgrims and the Indigenous peoples by violently attacking them with out simply trigger, which freaked everybody out and, I believe, probably began the ball rolling down a path that may ultimately result in the virtually full genocide of the Native People. So. Large yikes.
For a chew for lunch earlier than you head to the airport, take a look at Dillion’s Local in Plymouth. You’ll be able to’t go unsuitable with their fish & chips or Cap Cod Ruben!
After which, it’s time to go again to Boston to catch your flight. Boston is 45 minutes to an hour away from Plymouth, however be certain that to depart loads of time earlier than your flight as a result of visitors is unpredictable!
What to Pack for a New England Street Journey
One factor individuals both adore or despise about New England is that we’ve got very distinct seasons. You’ll must pack accordingly!
- Layers: Within the fall, the evenings and mornings can get very chilly, whereas daytime may be fairly comfy. Pack lengthy and brief sleeves, and skinny sweaters that may match simply underneath a fleece jacket or wool coat; that’s until you’re from Arizona, or planning to hike Mount Washington, then you may also need one in every of these packable down jackets. And you’ll want to pack just a few cute hats, scarves, and gloves for maximium fall cuteness and coziness! In the summertime, you most likely received’t want greater than a hoodie at night time, however convey a fleece jacket and windbreaker for the mountains.
- Bathing suit: You’ll be getting some good seaside time on this highway journey! However take into account a wetsuit should you’re planning on spending any severe time within the ocean. Even in summer time, common water temperatures stay within the 60s.
- Tevas or sneakers: You’ll need close-toed footwear for strolling alongside rocky seashores.
- Umbrella and rain jacket: We’re liable to 1-3 day stretches of wet climate any time, and scorching summer time days can produce explosive pop up thunderstorms.
- Mosquito and tick repellent: Essentially the most harmful animal in New England isn’t the moose, and even the good white shark, however the mighty deer tick. Because of the deer tick, which isn’t any bigger than a sesame seed, New England has the nation’s highest price of lyme illness. Pack a pair of pointy tweezers for safely eradicating a tick as soon as it has embedded in your skin. But when it makes you’re feeling higher, I’ve lived in New England most of my life and I’ve by no means as soon as had to do that.
- Mountaineering gear: You don’t must go loopy at LL Bean, however you’ll need trail sneakers or hiking boots; long, lightweight pants (due to the ticks), and a small day pack for water, snacks, and so forth.
10-Day New England Street Journey Map
We’ve created a map of this New England highway journey! It contains the itinerary highlights (i.e. the place you may be driving to and staying) in addition to the overall driving instructions (which embrace different areas simply so Google will take you the correct route). Put it aside for offline use in case your web or GPS cuts out. And you’ll want to bookmark this web page to refer again to whilst you’re planning!
About Our Contributor: Anna Laird Barto is a contract author who has lived in all places from Cuba to Wisconsin however is now primarily based within the wild west of Massachusetts. Her writing has appeared in quite a lot of journey, well being, and literary magazines together with Fodor’s, Hobart and Wanderlust. She helps her writing behavior by working at a non-profit household middle. To learn extra of her work go to annalairdbarto.com.
Are you able to hit the highway? Which cease on this New England highway journey itinerary are you most enthusiastic about? Tell us within the feedback beneath
Psst: Planning some East Coast getaways? Check out a few of our different posts!


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Our High Journey Suggestions & Assets
Listed here are our favourite journey suggestions & sources for saving cash and planning journey logistics! For extra suggestions, take a look at our travel tips resource page or our guide to planning a trip.- Reserving Flights: To attain flight offers, search on Skyscanner or Kayak. Cash-saving suggestions: fly mid-week or on the weekend; fly carry-on solely on a finances airline; and take red-eyes or early morning flights.
- Lodging: We often keep in budget-friendly, trip leases, boutique lodges or personal rooms in hostels. We use Booking.com to ebook lodges (we love their versatile cancellation coverage) and Hostelworld to ebook hostels (low deposit, simple change/cancellation, and wonderful critiques). For trip leases, we want to ebook utilizing VRBO (they have decrease charges and higher assist than Airbnb, and we’re not followers of Airbnb’s unethical monitor document.) You may as well ebook trip leases on Expedia and Hotels.com. We have additionally used TrustedHousesitters as each hosts (for our house and our fur-child) and vacationers!
- Journey Insurance coverage: We at all times, at all times, ALWAYS purchase journey insurance coverage for worldwide journeys, and we STRONGLY recommend it – go to our Travel Insurance Guide to search out out why. We suggest both World Nomads or SafetyWing for worldwide journey insurance coverage. SafetyWing is without doubt one of the few insurance policies that covers Covid-19, and so they have wonderful month-to-month insurance policies which can be good for Digital Nomads and long run vacationers!
- Vaccines & Meds: We use the journey guides on the CDC website to analysis really useful medicines and vaccines for worldwide journeys. We at all times suggest getting each vaccine really useful by the CDC! You may get them at your major care physician’s workplace or a walk-in pharmacy.
- Excursions: We love reserving guided excursions, particularly meals excursions and strolling excursions, to get a neighborhood’s perspective and a historical past lesson whereas sight-seeing! We ebook our excursions utilizing Viator and GetYourGuide.
- Transportation: We use Rome2Rio to determine tips on how to get from place to position utilizing public transit, and ebook native transportation on-line utilizing Bookaway wherever we will. After we ebook a rental automotive, we use Kayak to check rental firms and discover one of the best deal.
- Baggage Storage: Each time we’re testing early or making the most of an extended layover, we use Stasher or LuggageHero to soundly retailer our baggage whereas we’re working round. On Stasher, you need to use the code PW10 for 10% off!
- What to Pack: Here are the travel essentials that we convey on each journey. We even have packing lists for hot weather, cold weather, and plenty of extra. Check out all of our packing guides!
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