Hotels Trip Ideas water sky outdoor Boat boating vehicle Lake reflection River tied
Trip Ideas

7 Charming New England Towns We Love

You can't go wrong with New England—with its waterfront hamlets, sleepy harbors, fresh seafood... need we say more? Here, we're sharing our favorite under-the-radar towns from every state in the region for your ultimate trip through the Northeast.

Chelsea is Brooklyn-based travel writer, editor, and photographer. When not home eating her way through NYC, she's gallivanting across the globe, sailing the coast of Croatia or hiking the peaks of Peru. Her superpowers include booking flight deals and sleeping in small plane seats.

See recent posts by Chelsea Bengier

Trip Ideas grass sky building outdoor field stately home house château green estate landmark palace lawn Architecture manor house mansion facade monastery grassy castle old government building stone
Trip Ideas sky Boat outdoor water scene Harbor vehicle Sea dock docked ship marina port watercraft cityscape reflection day
Travel Tips Trip Ideas sky outdoor water lighthouse tower rock Sea Coast Nature Ocean cliff cape terrain
Classic Deck Elegant Hotels Inn Living Luxury Patio Scenic views Suite Trip Ideas indoor window floor ceiling room property furniture home living room estate real estate interior design hardwood farmhouse cottage condominium Design mansion
Lobster pots in Maine
Travel Tips Trip Ideas outdoor sky water rock shore River Sea Coast Ocean bridge reflection wave bay
1

Newport, Rhode Island

Gilded mansions. Windswept coastal drives. 17th-century captain’s homes. Newport is just as much a historic gem as it is Instagram gold. Start your day along Bellevue Avenue, the main drag of massive estates owned by wealthy families like the Vanderbilts (who referred to the chateaus as their "summer cottages"). Rosecliff, Marble House, and the grandest of them all, The Breakers are all worth touring, while the Cliff Walk, a path that winds between the manicured gardens and the sea below, provides another unbeatable view. If you want to stay in one of these grand homes, the Castle Hill Inn sits on 40 waterfront acres and has a private Hinckley yacht guests can use to cruise around Narragansett Bay. Next stop? Hit the town to explore the nautical shops along Thames Street and the fudgeries and seafood joints by Bowen's Wharf. On your must-do list: lunch at the Black Pearl, a cozy restaurant that looks like the cabin of an old ship and has the best clam chowder we’ve ever tasted. Come sunset, go for a drive along the winding Ocean Drive then end with dinner at the White Horse Tavern, a Newport institution that's been serving customers since 1673.

Food + Drink Outdoors + Adventure Trip Ideas Weekend Getaways indoor window living room room property condominium estate home interior design real estate ceiling Lobby floor Villa Design window covering apartment mansion Resort furniture
Country Deck Drink Eat Inn Patio Resort Trip Ideas tree table umbrella outdoor chair leisure tent Dining lawn canopy set restaurant outdoor structure area furniture shade several
Country Exterior Grounds Inn Resort Trip Ideas tree outdoor flower grass Garden lawn flora botany plant estate leaf yard botanical garden park backyard autumn landscape architect shrub landscaping
2

Woodstock, Vermont

This whimsical slice of Vermont is known for its thriving art scene, rich history, and locavore cuisine. Stay at the gorgeous Woodstock Inn & Resort, which puts you at the center of town so you can easily stroll along Central Street to Collective, or pop into Simon Pearce’s glassblowing workshop and flagship store just up the road in Quechee. Mon Vert Cafe dishes up a killer menu of gourmet paninis (try the Devil on Horseback with bacon, Vermont Creamery goat cheese, and walnut date spread) and morning brews (the maple latte is a must), while hidden gem The Prince & The Pauper serves mouthwatering meals like Tuscan lamb with Bordelaise sauce. Woodstock’s storied past is still prevalent: the First Congregational Church houses an 1818 Paul Revere bell that visitors can touch and beautiful covered bridges dot the landscape around the state’s only national park. Billings Farm and Museum offers tours and sleigh rides around the grounds (both are free to guests). Stop by the Woodstock Farmers Market or The Village Butcher for some authentic take-home treats.

RELATED: 8 Adorable Towns for Your Next Vermont Getaway

Trip Ideas outdoor rock ground water bicycle Beach Ocean rocky vehicle mountain bike Coast Sea vacation cycling parked mountain biking mountain sports equipment sand overlooking stone sandy shore
Trip Ideas water Boat outdoor sky vehicle Harbor Sea vacation boating marina dock Coast waterway bay docked floating
Trip Ideas indoor wall floor bed room Bedroom property hotel interior design home estate living room Suite real estate cottage furniture bed sheet Design apartment decorated
Trip Ideas color indoor room blue floor living room property window Living dining room home estate house interior design real estate green condominium furniture cottage Design Villa window covering apartment mansion Bedroom decorated area
3

Edgartown, Martha's Vineyard

As a former whaling port, Edgartown is one of the most quaint places on The Vineyard. Its pedestrian streets are lined with white shingled historic houses, blossoming hydrangeas, and charming restaurants. Start the morning at Among the Flowers Cafe or eat dessert first with a sweet treat in the secret garden patio at L’etoile (the Toasted Coconut Rum Crème Brûlée is to die for). Then enjoy the rest of the day at leisure, strolling the cobblestoned streets or getting cultured with a tour of local landmarks like the Old Whaling Church and the Dr. Daniel Fisher House. As for where to stay, the whimsical, coastal-chic The Christopher is the hippest new hotel in town—especially at night when locals and guests alike sip wine around fire pits in the plush courtyard.

Grounds Lodge Romance Romantic Rustic Trip Ideas Waterfront tree grass outdoor park Garden estate backyard home lawn flower yard woodland cottage plant
Living room at The Cottages at Cabot Cove, Maine
Romance Trip Ideas Weekend Getaways sky water outdoor pier Boat dock Sea vehicle vacation wooden Coast Harbor overlooking net
Exterior of a cabin at The Cottages at Cabot Cove, Maine
4

Kennebunkport, Maine

There are two reasons city-slickers escape to Maine: its rugged wilderness and its coastal hamlets. Make Kennebunkport your home for the weekend, and spend your time browsing the beach chic boutiques and exploring the windswept shores, studded with picturesque lighthouses. Outdoorsy types will love kayaking the Mousam River Estuary (where you’ll likely spot eagles and osprey) or trying their hands at lobstering from a 65-foot boat. Just make sure to save time for the bonfire dinner at Earth, where James Beard award-winning chef Ken Oringer whips up dishes like Birch glazed short ribs with pickled chanterelles. At the end of the evening, bed down in your own private abode at the Cottages at Cabot Cove.

Secret Getaways Trip Ideas food table plate dish meal Seafood fish lobster animal source foods seafood boil produce invertebrate container decapoda cuisine crustacean
Trip Ideas person blue sense food hand dessert
Secret Getaways Trip Ideas sky outdoor tree aerial photography bird's eye view landmark City River urban area tourism cityscape vacation flower park skyline day
Bedroom Boutique City Hip Inn Trip Ideas indoor bed wall floor room property ceiling window home hotel real estate cottage Suite interior design estate living room apartment
Boutique City Hip Inn Living Rustic Trip Ideas sofa room indoor floor Fireplace property chair furniture estate living room home Lobby interior design cottage stone real estate Design farmhouse Villa decorated
Hotels Trip Ideas water sky outdoor Boat boating vehicle Lake reflection River tied

Top left photos by Morgan Yeager

5

Portsmouth, New Hampshire

New Hampshire may be small, but it's full of adorable towns—namely Portsmouth. To really get a taste of its culture, go for the Prescott Park Arts Festival in the summer, where music, art, theater and dance performances take over the 10-acre park on the Piscataqua River. And don’t miss Portsmouth’s thriving culinary scene: Row 34 specializes in fresh seafood (the $1 oyster happy hour is a must) and the Ale House Inn is a brewery-turned-hotel that welcomes guests with local Smuttynose suds.

Food + Drink Trip Ideas food dish chip cuisine tostada guacamole vegetable dip rice snack food produce meal vegetarian food breakfast condiment different containing several variety
Trip Ideas table indoor cocktail Drink alcoholic beverage wooden distilled beverage beverage liqueur half alcohol glass
Food + Drink Luxury Travel Trip Ideas Weekend Getaways outdoor sky water Boat reflection Lake scene vehicle River boating loch reservoir landscape waterway Sea Harbor bay dock shore day tied colored
6

Falmouth, Massachusetts

When you picture a quintessential New England getaway, Falmouth is the first to come to mind. This village pulls out all the stops, with a charming green, a boutique-lined main street, and a white-steepled 19th-century church. Fashionistas will love the preppy-cool shops like Cape Chic, Vagabond Treasures, and Twigs while the kiddos can browse the books at Eight Cousins. When hunger strikes, pop into Anejo Mexican Bistro for the tableside guacamole and tequila. Or, if you’re feeling French, The Glass Onion serves classics like duck confit rillette, lobster strudel, pan roasted Atlantic swordfish. But make sure to save room for dessert at the town-favorite Ben and Bill's Chocolate Emporium, where locals line up around the block for a scoop of the homemade buttered lobster flavor (this is New England, after all).

RELATED: 6 Underrated Fall Getaways from NYC 

Book Hotels in Massachusetts
Food + Drink Travel Tips Trip Ideas cup coffee table person indoor Drink beverage food latte caffeine caffè macchiato espresso ristretto cappuccino sense flavor drinking
Trip Ideas wood furniture art tourist attraction interior design home museum table restaurant antique shelf old cluttered
Trip Ideas indoor room home interior design living room furniture lighting Design table dining room cluttered

Bottom photos by Nancy Kirkiles, courtesy of Weekend Kitchen

7

Essex, Connecticut

Blink and you might miss this tiny Connecticut hamlet, which is made up of an idyllic main street, a sleepy riverfront harbor, and rows of traditional New England-style homes. Once you get here, check into the Griswold Inn, a 1776 bolthole said to be America’s oldest continuously operating inn. The whole place feels like a blast from the past, with a wood-paneled tap room, a roaring fireplace, and guest rooms decorated with antiques and nautical oddities. Down Main Street, you’ll find Essex Coffee & Tea for pastries and a cappuccino, Weekend Kitchen for vintage houseware and cooking classes, plus Truffle Shots for a killer Macallan 12-year Scotch, caramel and dark chocolate ganache shot.

Charming New England Dress Outfit

For info on these editor-selected items, click to visit the seller’s site. Things you buy may earn us a commission.

Want more?

Comments

comments

All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.