55 Surprisingly Romantic Getaways in New England

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“Romantic Escape” may not leap to mind when you come across some of these destinations in New England. But the following 55 ideas might just open your eyes to new places to explore together. From snug B&B’s to urban hotels, revitalized cities, and quiet lakeside resorts, you’ll find something just perfect for the quirky, fun-loving, luxury-seeking couple. For the complete list of our choices for Romantic Getaways from Virginia to Maine, check out this list.

CONNECTICUT

CHESTER/HADDAM, CT ON THE CONNECTICUT RIVER: Performing, fine and culinary artists, as well as clothing and building designers have been drawn to this mesmerizing ribbon of water, the Connecticut River, for centuries and after indulging in this Getaway you’ll see why. Some of the best artists and chefs in the region create in local kitchens and studios and since it reopened in 1968, the Victorian confection that is the Goodspeed Opera House has sent 19 productions to Broadway. See a musical, shop in one-of-a-kind (inexpensive) designer boutiques and end the day with an exquisite meal.CLINTON/MADISON, CT: no fudge shops or glitz and glamour here – just serpentine rivers, a quaint harbor, an anachronistic winery, a rustic flower and animal farm, one of the most highly regarded indie bookstores in the country, Connecticut’s only beachfront lodging – The Madison Beach Resort – and the best lobster roll on the East Coast (Lobster Landing/Clinton).

CONNECTICUT’S NORTHEAST CORNER: Sweethearts who enjoy discovering the newest “hot spot” together will love this formerly industrial section of Connecticut, with a growing art district and, ironically, plenty of nightlife.

CONNECTICUT’S NORTHWEST BORDER:  There’s a reason some of our favorite celebs have homes up here. Far from the maddening Hampton’s Season, the pace in this farmland and lakes section of Connecticut is slow and quiet. Quiet, that is, except for Lime Rock Racetrack (preferred by Paul Newman until he couldn’t race anymore in his early 80’s). You and your lover will love Falls Village Inn, with rooms done by NY City Interior Designer, Bunny Williams.

GREENWICH CT: This swanky Connecticut town is so much more than just the center of the Preppy Handbook universe. Known for its hedge fund billionaires, Captains of Industry and Hollywood types, Greenwich does not broadcast its considerable tourist assets, many of which, ironically, are inexpensive or free. Why is it on this “Romantic Spots” list? Because of J-House, a high-tech, artsy, green former Howard Johnson’s that has just unveiled the brand new J-Spa encompassing one former guest room gutted and now dedicated to Couples Spa Treatments. J-House is  the only boutique hotel in town and such a Maven Favorite, it’s earned its own review HERE.

HIDDEN VALLEY B&B, WASHINGTON DEPOT CT: This is one of the most romantically situated B&B’s in the world – perched over the Litchfield Hills. Every room in this Dutch Colonial house on the hill is a delight for the eyes. And just wait till you see the expansive and breathtaking stone patio. Just a couple of hours from NYC, it’s worlds apart.

INTERLAKEN INN, Lakeville: Romantic and pastoral in Connecticut’s lake district.

Winterberry Holly Chatfield Hollow SP Killingworth CT

KILLINGWORTH: Lovers with a penchant for lavender, long walks in the forest, and staying in a hidden hip 5-room B&B on a gourmet mushroom farm will plainly adore a quick trip to Killingworth CT and the Chatfield Hollow Inn.

OLD LYME, CT: Morning fog in Old Lyme CT transforms the landscape into the hazy tableau of an impressionist painting in the very place considered the Birthplace of American Impressionism. In the late 1890’s, widow Florence Griswold opened her home to American artists fresh from studying in France, forming the country’s first European-style Art Colony – an “American Giverny”.  Witness dreamy sunrises, wander through art galleries, and dine on outstanding cuisine surrounded by art at the Bee and Thistle Inn on this Fine-Arts Getaway.

OLD SAYBROOK, CT: Situated at the mouth of the Connecticut River where it meets Long Island Sound, Old Saybrook CT has drawn vacationers and celebrities for 150 years. Wavy-voiced actress, Katharine Hepburn lived in the Fenwick neighborhood until her death in 2003. Out on “the point,” The Saybrook Point Inn and Spa just opened Three Stories – its new “Boutique Inn” –  in addition to the hotel’s already luxurious accommodations. Learn about Saybrook Point’s earlier incarnation as Terra Mar, frequented by Hollywood luminaries and gangsters, and some cherished African American history on this surprisingly down-to-earth but high-class Connecticut coastal Getaway.

WETHERSFIELD CT: If you and your honey love to curl up with the latest Revolutionary War history book, get all gooey eyed over George Washington’s sleeping quarters, or even fantasize about growing Heirloom vegetables from seeds,  you’ll love meandering around this very Historic District, just a few miles from Hartford, which offers two charming B&B’s, great restaurants, authentically restored pre-and-post Colonial homes, and two of the oldest packaged seed companies in the USA still in operation.

RHODE ISLAND

NARRAGANSETT RI: Those who believe that New England beach resort towns are dead in the wintertime must visit Narragansett RI – a popular Atlantic Ocean beach community – in the coldest months. For starters, January is the best month for surfing (who knew?), down-filled outerwear is made for brisk strolls on snow-covered sand, favorite restaurants still buzz with happy eaters, shops are open, and best of all, rates at the coolest new boutique hotel, The Break, are satisfyingly low. So bring your Polar Bear honey to the Rhode Island shore for a bracing, romantic getaway.

NEWPORT, RI: Newport RI has a flair for the dramatic. The town is both paean to the America’s Cup Yacht Race and the conspicuous consumer lifestyle of the Gilded Age, with lots of shopping, great restaurants and the prestigious Relais & Chateaux’s Castle Hill Inn – an out of town hideaway with the most enthralling views of the Atlantic Ocean from almost every balcony or deck.

WATCH HILL RI: Victorians came to this seaside town, with their steamer trucks, for a summer of relaxation. Taylor Swift loved it so much, she bought a house here. Plus, there’s an oyster farm, great brews, sand, and surf. And, if you really want to impress your sweetheart, stay at the ultra-luxe Ocean House hotel, which has recently updated its rooms.

MASSACHUSETTS 

FALMOUTH/SEACREST BEACH HOTEL: Falmouth MA, in the extreme southwest corner of Cape Cod, also encompasses the tiny burg of Woods Hole.  But there are things to see in Falmouth as well, including a recently renovated Victorian mansion turned art museum, waterfront gardens with antique anchors as central features, and some of the country’s most awesome sunsets – right from a newly renovated beachfront hotel resort with rates that won’t drain your bank account. Sitting on a beach chair with a glass of wine, waves gently tickling your feet as the sun goes down, you might just be inspired to give her that ring.

Working docks Gloucester MA
Working docks Gloucester MA

GLOUCESTER MA: Lost in all the “Perfect Storm” commercial fisheries identity is the fact that this coastal New England town was also one of America’s first Artist’s Colonies –  Rocky Neck – and what’s more romantic than that? Stay in a boutique hotel, tour the eclectic home of one of the very first professional interior decorators, and drink some great beer overlooking the fishing docks on this not-so-fishy getaway.

HIDDEN BOSTON MAHipster couples will want to check out these secret spots in Boston. And then bed down in the city’s newest rock ‘n roll (slightly bad-ass) boutique hotel – The Verb, right in the shadow of Fenway Park. Even Bostonians don’t know about some of these places.

MARTHA’S VINEYARD, MA: This New England Island- a ferry ride from Wood’s Hole, MA, delivers on hypnotic sunrises and sunsets, exceptional beaches and intimate hideaways. Even if you aren’t president of the United States, you’ll be treated like one.

NANTUCKET:  Islands are just naturally romantic, given that you’ve got to take a boat or ferry to get there. Honeys with a curiosity about American Maritime and Whaling history are sure to find cerebral satisfaction in this preppy place – home to one of the best Whaling Museums in the world, and of course, the iconic Nantucket Lightship Basket. Stay at the Regatta Inn on a little side-street: what rooms lack in size are more than made up for with impeccably luxurious design.

Costumed Docents at Plimoth Plantation

PLYMOUTH MA: Lovers of history (and each other) will go gaga over the very first New World sanctuary for “Saints” who were religiously persecuted in Europe in the early 1600’s. The year 2020 will surely be a whirlwind of celebrations as Plymouth celebrates the 400th anniversary of the landing of the Pilgrims on Plymouth Rock.

PROVINCETOWN MA: Live on the edge on this edge-of-the-world resort town. LGBT couples will find nirvana (and a whole lot of choice re: accommodations), but hetero romantics (and families) will also have a great, high-energy time at the tip-end of Cape Cod. Whether you’re gay or straight, one of the most stylish inns to book is Carpe Diem Guesthouse, with gorgeous rooms, bountiful complimentary afternoon wine and nibbles, a fantastic breakfast spread, and the largest Moroccan Hamam on the Cape.

ROCKPORT MA: You live in Boston or New York, and you both long for a seaside escape with lots of fresh lobster, but just don’t want to drive all the way to Maine. What to do? Head to Rockport MASS – which provides LOTS of New England Coast charm without the hassle. Stay at Yankee Clipper Inn – favorite of many celebrities of yore – a few miles from town on a wind-whipped cliff overlooking the Atlantic. It’s as romantic as all get out.

NEW HAMPSHIRE

HANOVER NH: Are you a pair of through-hikers on the Appalachian Trail, a bit tired of camping out, and looking for some luxe digs for one night? You’re in luck. Just 431 miles from its northern end in Katahdin ME (1,713 miles from its starting point in Georgia), the trail runs right by the front door of the newly renovated Hanover Inn, basically on the Dartmouth College campus.

MANCHESTER NH: New Hampshire’s largest city not only spawned some of the great comedians of our day  – Adam Sandler, Seth Meyers and Sarah Silverman – it gave innovators in wine (LaBell Winery) and chocolate (Dancing Lion Chocolate) a place to experiment and thrive. Hmm… wine and chocolate….? If you’re the kind of sweethearts who are into confections and fruit of the vine, or who gravitate to quirky and charming turnaround industrial towns, Manchester is a must. Sure you can stay in any number of franchise hotels – but you’ll want to bed down in the absolutely adorable Ash St. Inn, just a block from the famed Currier Art Museum.

Oceanic Hotel, Star Island Isle of Shoals NH
Oceanic Hotel, Star Island Isle of Shoals NH

PORTSMOUTH NH: Perhaps more than in any other New England seacoast town, it’s easy to imagine what life was like in this country when it was new and growing thanks to Portsmouth’s living history museum, Strawbery Banke, which isn’t a “museum” so much as a collection of 32 homes and establishments, most in their original locations and manned by costumed guides who interpret the lives and duties of the actual families who lived and worked in them. Just one of the draws of Portsmouth, this romantic seacoast town is also known for great dining, fun shopping and the Martin Hill Inn, voted “Best Garden Lovers B&B in New England” by Yankee Magazine.

Chesterfield Gorge NH

SOUTHWEST CORNER/KEENE/PETERBOROUGH: Lovers with a fondness for unexplored (or less explored) territories will want to escape to the area of New Hampshire that screams “New England” (so much, in fact, the region’s prime publication, Yankee Magazine, is based here). You’ll find Little Red Riding Hood’s “Grandma’s House,” the boyhood home of “Uncle Sam,” breathtaking hikes, Ken Burn’s restaurant, and one of the most charming Inn’s in the State – The Chesterfield Inn.

SQUAM LAKE AND LAKE WINNIPESAUKEE NHThe most iconic old-age romance movies of all time – On Golden Pond – was filmed right on Squam Lake (which served as “Golden Pond”), but lovers of all ages will appreciate the quiet beauty of Squam or the more active spots around the larger Lake Winnipesaukee. Stay at Manor on Golden Pond for classic elegance, afternoon tea and superb lake views.

WHITE MOUNTAIN REGION: The White Mountain Region in New Hampshire is so vast, the Getaway Mavens broke it down into three sections. Each area encompasses attractions old and new (mostly old) – perfect for the hiking couple seeking fresh mountain air and classic, old fashioned resorts and hotels. Some, as you will see, score highly on the “Romance” scale.

 VERMONT

BENNINGTON VT: This was Robert Frost’s “Road Less Traveled” and in fact, America’s famed rural poet is buried in this Vermont burg just over the Massachusetts border. The lush, green surrounding mountains are the defining aspect of this region – inspiration for poets and artists like Frost, Grandma Moses and Norman Rockwell. And for poetry-spouting twosomes as well. Stay in finery in a grand Federalist inn, The Four Chimneys Inn – perfect for the couple seeking a Victorian-age “summer in the mountains” experience along with lightening fast wi-fi access.

BURLINGTON VT: He loves Teddy Bears. She loves beer. And you both love sunsets over a placid mountain lake. Presenting – Burlington, known as home to University of Vermont and a growing number of micro-breweries. Not to mention Vermont Teddy Bear Co. Choose between two very different accommodations: the fun, quirky 4-room Mid-Century Modern decorated Victorian B&B, Made Inn Vermont, or larger stunning contemporary boutique hotel, Hotel Vermont. Both stress the craft beer experience – Made Inn Vermont treats each guest to a can of Heady Topper and Focal Banger, Hotel Vermont keeps a “Beer Concierge” on staff to direct guests to the best breweries in the area (and even offers a full-day, two night Brewery Tour package every other week).

FOUR COLUMNS INN, NEWFANE VT. Renovated in 2014, and reopened in 2015, this world-renowned New England Inn drew the likes of Mick Jagger (he and Jerry Hall stayed here for his both b’day) and other Boldfaced Names back in the 80’s and 90’s. Not resting on its laurels, the inn has all the elements necessary for a romantic getaway: fantastic food in on-site Artisan Restaurant, a funky pub, and eclectically charming and luxurious rooms. You’ll never have to leave the stunning property if you don’t want to.

LUDLOW/OKEMO VALLEY: The bulk of visitors come to Okemo Valley to ski – Okemo is, after all, one of the top ski resorts in the Northeast. But like all other Getaway Maven escapes, this one does not focus on the “One Obvious Thing.” The Okemo Valley Region is comprised of 14 little villages (Ludlow being the largest, followed by Weston and Chester). There is just one traffic light – in Ludlow – and no box stores. You can sign up for a 2-day crash craft-course, wander the halls of one of the first co-ed Academies in the country (now a great museum), shop like a fiend, eat like a foodie, and stay glamorous in a “castle” built by a Vermont Governor – the very baronial and stunning Castle Hill Resort and Spa.

MANCHESTER: This escape is tailor-made for the outdoorsy, adventurous couple. Once known for its Outlet Stores and golf at the age-old Equinox Resort, Manchester VT is transitioning into a four-seasons soft adventure, “Sporting Weekend” hotspot with opportunities to learn extreme off-road driving (Land Rover Driving School), fly fish on some of the country’s best trout rivers (Orvis), and practice your shooting skills without killing anything (Covey & Nye) – all guided by experts in each field. There are plenty of places to stay, but all Kimpton fans will be happy to learn that The Taconic, Kimpton’s first property outside of a city, opened in Manchester last year. So, bring your dog and your sense of adventure. Both with be glad you did.

MIDDLEBURY VT. Horse-lovers, beer and wine lovers, or just lovers in general will love Middlebury. The College campus even has its own LOVE Sculpture. Stay at Inn on the Green, and you can snuggle up while enjoying breakfast in bed.

RABBIT HILL INN, LOWER WATERFORD VT: Leave it to the 19-room Rabbit Hill Inn  to make log-pine luxurious. The Cedar Glen room, kited out in Adirondack-chic, is an elegant blend of pine and plaid, and one of the most difficult rooms to leave once settled in. But this is not the only reason the Rabbit Hill Inn has been among the top lodging establishments in New England: any country inn can be prettied up. No, Rabbit Hill is tops due to its owners, Brian and Leslie Mulcahy, who have been here 23 years, and exude the kind of warmth and good will that radiates brightly around them. Sure, you can sequester yourselves in a charming room here and never emerge, but RHI is best for happy couples who love to socialize and make friends. It’s got that kind of vibe.

RED CLOVER INN, MENDON VT: Only 15 minutes from Killington Ski Resort, Red Clover Inn – quiet, lovely and oozing romantic appeal – is a secluded hideaway for skiers who want a break from the crazy crowds on the hill.

THE ESSEX, VERMONTS CULINARY INN AND SPA: Ideal for the foodie couple who yearns to learn to cook together in a professional kitchen with professional chefs, dine on terrific, innovative cuisine and stay overnight in comfy quarters. This property was once a satellite campus of the prestigious New England Culinary Institute until 2009 (when the Institute was consolidated in Montpelier), with the teaching ethos, training kitchens and equipment intact. Since then, the resort has built a world-class spa, kitchen gardens, a beautifully landscaped pool, and is in the process of upscaling guestrooms. With two great restaurants on site – not to mention private kitchens for that “special” event (proposals, anniversaries, etc.) – The Essex is a unique destination resort.

WILMINGTON VT: Lovers of a certain age will remember spending weekends at Mount Snow (or Haystack) back when  Poncho’s Wreck in Wilmington was the place to go after a day on the hill. Several years ago, Hurricane Irene wiped out most of the town, including Poncho’s. Though that restaurant is no more, plenty of other new highly regarded locally sourced restaurants are. If your days of attacking the mountain are behind you – and you’d like a few runs in the morning followed by puttering around town and eating well, stay at the Wilmington Inn and Tavern, and see how Wilmington is back!

WOODSTOCK VT: Once a release valve for the Victorian wealthy who’d take the train from NYC or Boston to White River Junction, and then the 14-mile spur into the mountains, Woodstock feels romantically lost in time. This is the region where where the National Park Service chose to impart the history of land conservation in the US. Add to that great hand-crafted cheese, famous artisans, and a historic luxury inn, and you’re golden for a wonderful cozy weekend. Plan to stay or at least book spa treatments at the uber-friendly and recently updated Woodstock Inn and Spa – the town’s centerpiece lodging.

MAINE

BANGOR ME: Have you and your guy/gal bonded over Steven King? Then, get thee to what King calls “Derry ME” in many of his novels. Of course, there’s a Steven King Tour available in Bangor, some great shops and restaurants, and a brand new Residence Inn by Marriott with the coolest double showers ever.

BOOTHBAY ME: Boothbay Harbor ME was the first “off-Route-1 town” that became popular with tourists on the Maine Coast, and, centered in “Mid Coast Maine” is quicker to get to than Bar Harbor and Acadia National Park to the northeast. Yes, tourists converge here in the summertime, but plan a trip in June, and you’ll get the best of all worlds: temperate weather, phenomenal blooms, uncrowded attractions, and lower hotel rates. There’s a reason Boothbay Harbor and the adjacent Boothbay ME became so popular – collectively, it’s stunning.

CASTINE AND BLUE HILL PENINSULA ME: And, here’s more for the crowd-averse couple. Far off the well-trod Route 1, visiting Castine ME and the Blue Hill Peninsula is another great escape from the hordes. Just an hour from booming Bar Harbor, time seems suspended here, especially around Castine’s Town Green– a whitewashed series of buildings that include the Unitarian Church, Town Hall, and Historical Society – and the waterfront, not much more than a couple of restaurants and docks.

CLIFF HOUSE, Cape Neddick. Starry eyed twosomes seeking the hottest hotel on the East Coast will discover it here. InStyle Magazine called the re-imagined Cliff House on Cape Neddick ME one of the best spots in the world to get engaged, and when you drive past lovely shore homes, pull into the long drive, and at last enter this Oceanside resort perched on rocky Maine cliffs, you’ll understand why.

FREEPORT ME: Love to shop? LL Bean, open 24/7, is headquartered here. And you can stay in Ole Yankee luxury at the Harraseeket Inn.

FRYEBURG ME: There’s not much going on in this New Hampshire/Maine border town, yet it is one of the Maven Favorite romantic destinations. Why? The Oxford Inn – an upscale, four room B&B with two outrageously good restaurants (one a pub), with one of the most stunning views on this list. Go in Autumn when the foliage turns the hills ablaze with color.

GREENVILLE ON MOOSEHEAD LAKE ME: If your love loves to take photos of moose – or criss-cross snow-covered logging roads on a ski-mobile, a visit to this Northern Maine town is in order. Greenville Inn is snug, cozy and luxurious all year long, but particularly lovely in winter.

INN BY THE SEA, CAPE ELIZABETH ME: I was told not to write about this luxurious big-dog friendly environmentally “green” inn by repeat visitors who’d like to keep it their secret (and not be blocked out of rooms). The best choice on the East Coast for dog-loving duos.

KENNEBUNKS,ME: In the Kennebunks, you will find the freshest New England cuisine, transcendent ocean-scapes, the light, the sea at play against the rocky shore. All that makes Maine Maine is here, but on a much smaller, less touristy scale. Plan to go in the warm months of June or September, when sightseers don’t overrun the place and you can find parking and reduced hotel prices mid-week.

LUBEC ME: This Getaway, to Lubec and Eastport ME, and FDR’s summer cottage on Campobello Island, brings you to the easternmost land in the United States, with a short foray into Canada. Yes, it’s all the way up here. Or Down Here – to coin a “Downeast” phrase: a good ten hours from New York City or 7 from Boston. But so totally worth it. It’s beautiful and welcoming, especially to cute couples, but be sure to bring your Passport!

MIGIS LODGE, Sebago Lake. If loon calls at night thrill you no end, and the thought of a crackling fire in the living room of your own luxury cabin sets your heart ablaze, this lakefront resort is a perfect fit.

MONHEGAN ISLAND: Ten miles off Mid-Coast Maine, Monhegan Island is known for its artists and lobstermen, who live, symbiotically, on this tiny crust of land just under a square mile in size. Though the population dwindles to 50 year round, when lobstermen continue to pull in those popular Maine crustaceans, warm weather brings artists, writers, birders, nature lovers and curious tourists who don’t mind experiencing a simple life without cars (or paved roads), private bathrooms, or even, in some cases, electricity. But, ah, those views: The views that inspired some of America’s most famed artists. Those are what you came for, anyway.

PHIPPSBURG PENNINSULA ME: The Sebasco Harbor Resort becomes a multi-generation hub in the heat of the summer, but come off season, and this waterfront resort is prime for romantic couples seeking peace and quiet. Plus, there’s more to explore just 20 minutes away.  The phenomenal Maine Maritime Museum is located in Bath – still home to mega-boat-builder, Bath Iron Works. But Bath is just 10 minutes from one of the best college art museums in the country – Bowdoin Museum of Art.– So, gear up for a great getaway full of American History, Art, and Recreation on this often overlooked portion of Coastal Maine.

ROCKLAND ME: For the art-aficianoados who love Wyeths and lobsters, and a chance to stay in a hot new boutique hotel.

SCHOODIC PENINSULA ME: Are the two of you in sync about nature and hiking but hate crowds? Infinitely more secluded, Schoodic encompasses 3,500 additional acres of Acadia National Park, with ferry and bus access to the bulk of it on Mount Desert Island. The small towns of Winter Harbor, Birch Harbor and Prospect Harbor are all located on Schoodic, so on this Getaway, you’ll experience nature in its rustic glory, and if you’re game – a few “Pickled Wrinkles.”

SEARSPORT AND ISLESBORO ME: Dine in intimate splendor and stay at a grand Sea Captain’s mansion, and then poke around a sleepy island just offshore on this unique lesser-known-Maine getaway.

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