11 of the Most Quaint Small Towns in New England
Why New England? Well, the name of the region comes not only from the first English settlers but also because it resembled their homeland, with its sweeping coastal landscapes and dramatic bluffs. Consider the charming town of Chilmark, which exudes quaint Irish vibes. It's no wonder the feel-good series 'Gilmore Girls' was inspired by Washington, Connecticut.
In Essex, you can bike from the countryside along winding, quiet streets to the colonial-style waterfront bustling with dockside activity. Whether you’re coming for a summer-dedicated vacation of watersports, a scenic fall foliage road trip, or a Saturday escape from the chaos of life, these villages will energetically replenish you with scenery.
Block Island, Rhode Island
Block Island exudes quaintness with its quiet, unspoiled white-sand beaches and pristine nature trails. You can commune with nature in the serenity of places like 1661 Farm & Gardens, home to camels, llamas, and lemurs, situated near thirty miles of scenic hiking trails. The small town near the Mohegan Bluffs offers unparalleled vistas from 200 feet above the ocean. Descend 141 steps, and you'll find yourself on a beautiful, secluded beach.
Nearby sprawls the birding hotspot for migratory species, the 46-acre National Wildlife Refuge of sandy beaches, and rolling dunes next to the crystal-clear Sachem Pond. Rodman’s Hollow, a 230-acre glacial outwash basin, overlooks the Atlantic and is rich in native flora. It features trails leading to Fresh Pond and Black Rock Beach, while the 120-acre Lewis-Dickens Farm Wildlife Refuge offers up farming history and level coastal meadows for hikes in a falconry and raptors habitat. Even Ulysses S. Grant, Franklin D. Roosevelt, and Bill Clinton fell in love with this tiny island's low-key vibes during their stays at the historic Atlantic Inn, known for its picturesque ocean views. Hop on a bike to explore the charming town's boutique-lined streets, where food and drink establishments offer views of the ocean and spectacular cliffs.
Camden, Maine
Camden, Maine, the coastal jewel on Penobscot Bay, is a summertime sailing mecca, with just the right amount of activity during the other seasons to enjoy its captivating arts scene and indulgent dining amidst tranquility and ocean breezes! Brimming with opportunities for outdoor adventure and ways to unwind along Main Street, the small town fulfills Maine’s slogan of “the way life should be!” In between visits to galleries and adorable boutiques like the Smiling Cow, the Cashmere Goat, the Owl & Turtle Bookshop, and the Leather Bench, you can enjoy dining and shopping for decor and gifts.
Autumn is spectacular here, especially when heading towards Mount Battie, with its 1.4-mile trail leading to the summit offering a hawk's-eye view of Camden and the islands of the bay! Don't miss the quiet nooks for afterwards, to watch the boats and down a lobster roll, perfected to an art here. There's Barrett's Cove, a freshwater beach on Megunticook Lake that's serene year-round, while the pretty library north of the shopping district is complete with a lawn, benches, and harbor views. Sit back, relax, and take in the collection of photogenic schooners, sailboats, and yachts that attract mariners from across the world!
Chatham, Massachusetts
This historic town, established in 1712 and now a regional shopping destination, blends old-fashioned charm with trendy eateries and art galleries, nestled among historic inns and white-steepled churches. Check out the 3,000+ collection at the Atwood House Museum of paintings, decorative arts, maritime artifacts, photos, and 19th-century nautical charts! Nestled on Cape Cod and bordered by water, this 16-square-mile town on higher ground offers days of tranquility, unsurpassed beauty, and endless views.
Don't miss the bustling commercial fishing pier set against Chatham’s stylish backdrop, complete with seals, the iconic Chatham Lighthouse, and model locomotives from the 1939 New York World’s Fair at the Chatham Railroad Museum housed in the 1887 train depot. Chatham, an ambient maritime escape, comprises pristine beaches for lounging and exploring, from the nearby circular coves and miles of saltwater inlets to the tidal shoals, fleeting sandbars, and wild barrier islands.
You can explore the chic boutiques and quaint storefronts along the dynamic, winding Main Street, where festivals explode in decorations and local cheers during the annual 4th of July Parade or the Chatham Christmas Stroll. Celebrate by Oyster Pond during 'First Night,' featuring fireworks and the traditional 'Dropping of the Cod' at midnight, or mingle during the Chatham Band Concert at Kate Gould Park under the moonlight, lamp-lit glow, and colorful balloons!
Chilmark, Massachusetts
This Martha's Vineyard town, nestled in a landscape that seems to float above the ocean offering endless views, evokes a sense of Ireland. It's unsurprising that the scenery here inspired the name, reflecting the area near where Thomas Mayhew Sr. was born in England. While the island's popularity surges in the summer, with many vacationers heading to Oak Bluffs, this rural part of the island remains a pleasantly subdued setting for a quintessential New England beach getaway. You can enjoy all-level hikes and island photography, with various landscapes, stunning coastlines, and sun-kissed waters always within reach.
The historic town of Chilmark, established in 1671, thrived with farming through the 19th century into an outdoor destination, while its authentic New England fishing village of Menemsha remains under the aura of bygone centuries. You can wander through small shops and eateries up to Beetlebung Corner at the center, home to a modern library and a chocolate factory. There's nothing better than Menemsha Fish Market to get the local feel for culture and try the best lobster rolls with chowder. Mark your calendar for the upcoming Martha’s Vineyard Film Festival in March here in town, the birthplace of Martha’s Vineyard Sign Language in the early 18th century!
Edgartown, Massachusetts
Exuding quaintness, Martha's Vineyard, located seven miles off the coast of Cape Cod, feels like a world apart. Edgartown, the picturesque harbor town on the eastern side, contributes significantly to the island's serene natural scenery. With activities ranging from walking and hiking to biking along its extensive trails, you can enjoy a morning run with spectacular views and an evening stroll along the same paths. In the hospitable downtown area, along with tips on exploring the surrounding open spaces, you can book a tour of historic properties featuring restored architecture and landmarks, including the Old Whaling Church and the Dr. Daniel Fisher House.
Once a whaling port, now bustling as a year-round destination, the seaside village lures in visitors with its classic New England flavor to its scenic harbor, with a delightful mix of old-world charm and modern amenities. From alluring pristine beaches to historic architecture, boutiques, and fresh-from-the-farm ingredients on tasteful menus, Edgartown caters to tourists in every season, warmly welcoming you to join in the fun at the Pink & Green Weekend in May and the 4th of July Fireworks & Parade. There's always something for everyone, from the Bass in the Grass event in September to the Martha’s Vineyard Food & Wine Festival in October, and don’t forget to mark your calendar for next year's Christmas in Edgartown!
Essex, Connecticut
Quaintness prevails in this small historic town, embraced by three water bodies, offering expansive views for miles. Postcard-like from all sides, the town extends into the Connecticut River, not like a sore thumb, but rather as a charming and officially recognized 'Perfect Small American Town.' You can drive or ride a bike a few miles south to Old Saybrook, which is ideal for scenic hikes offering rewarding views, where the river meets Long Island Sound.
Out here, "all roads lead to the Town Dock," with something for everyone to enjoy in scenery, like the adjacent historic 1878 warehouse turned Connecticut River Museum with exhibits, eagle tours, and special events on the sprawling lawn at the water’s edge. From regular parades and concerts to other small-town staples, quaint shops sit side-by-side with early Colonial and Federal-era homes. The Griswold Inn, also known as 'The Gris,' is reputed by the New York Times to be the 'oldest continuously operating inn in America.'
Freeport, Maine
If quaint to you means a respite from the gray city, work, or daily routine to reserve some time for yourself, then the historic village on the shores of Casco Bay is just the place. True to its name, the port town offers inspiring views and outdoor adventures, with world-famous outfitters located amidst other outlets, boutiques, and local shops. Famous for hosting the L.L. Bean headquarters, you can visit the flagship L.L. Bean store in Freeport, which offers more than just shopping—it's a complete experience!
Whether you're in for one of the festivals and events, over 3,000 acres of preserved lands marked for fresh air exploits, or seeking a quiet stroll through some pretty art galleries, you can stay, play, and most importantly, feel energetically replenished! Serving only fresh and local fare, the restaurateurs in Freeport pair regional favorites and seafood with an active craft brewing scene. Wolfe’s Neck Farm delights families with free admission and various programs, while the nearby towns offer just a short scenic journey to explore more of New England's beauty, especially during the fall foliage season.
Kennebunkport, Maine
While 'quaint' can mean different things to different people, in Kennebunkport, you'll find a getaway that seems tailored just for you. Whether you're into homeware shopping at Farm + Table in its distinctive red wooden barn, or you prefer boutique shopping, Summer Street is an architectural showcase featuring Federal and Colonial buildings. You can enjoy tranquility with down-to-earth ventures such as visiting Goat Island Light, one of Maine’s oldest lighthouses, and exploring Gooch’s Beach, situated along the Victorian-lined Beach Avenue. Just a few miles from the central Dock Square, the picturesque and tiny fishing village of Cape Porpoise hums at its own pace, with fishermen absorbed in their trade.
You can tour the National Historic District and the Brick Store Museum, while the three-mile-long serene Goose Rocks Beach is just 10 minutes north to deep-breathe sea salt air and relax, immersing yourself in the scenery. Heading south along the main road, the extraordinary 18th and 19th-century landmarks like the Lexington Elms, Horace Porter House, and Benjamin Brown House reflect the 'Hamptons of the Pine Tree State' moniker. From the lively downtown to the dramatic shoreside mansions, Kennebunkport is chock full of art galleries and patio cafes to unwind while people-watching, or enjoy some fried clams and lobster rolls at The Clam Shack.
Newport, Rhode Island
"America’s First Resort," Newport welcomes families, solitude-seekers, and worldwide travelers in search of a quaint escape that feels like coming home. A sought-after destination for nearly 400 years and recently named one of the nation's top destinations, Newport offers an 'aquatic playground' on all sides, once a haven exclusively for the nation's wealthiest. Today, you can certainly enjoy all the water pursuits you want and drool over the famed Newport Mansions, among other beautiful architecture, historic sites, and thrills for all.
Start your visit at the Brick Marketplace, then make your way to the adjacent, picturesque Thames Street, lined with delightful shops and restaurants. Enjoy gallery hopping, shopping, and dining at diverse restaurants. You can also take a self-guided tour of several Gilded Age mansions and enjoy the popular audio tour at The Breakers. Play a match or explore the International Tennis Hall of Fame for insights, then embark on a sailboat from the easily walkable waterfront to view the Christmas-decorated mansions and the stunning cityscape from the water.
Washington, Connecticut
Washington, a vibrant town, offers a blissful escape into a small-town pace with local businesses and a diverse cultural scene. Spread across five picturesque villages embraced by nature, you can explore arts and culture, world-class shopping, farm-to-table cuisine, and nearby natural attractions like Lake Waramaug, the Shepaug River, and the Litchfield Hills. Washington's quintessential New England ambiance and laid-back vibe extend into the stunning countryside, which beguiles with farm visits, vineyards, and rolling hills. Quaint hidden inns dot the winding countryside roads, set against the backdrop of the Berkshire Mountains.
Home to around 4,000, the friendly community comes together, extending a warm welcome to join during the Harvest Festival and the Holiday in the Depot. The town, reminiscent of Stars Hollow from 'Gilmore Girls,' was the actual inspiration for the show, with its small-town charm, excellent restaurants, gourmet markets, and the Mayflower Grace hotel, which inspired the Independence Inn where Lorelai Gilmore worked. Artists, musicians, and writers rejoice in the natural surroundings, whose fever you can in turn admire at several fabulous galleries with art of all mediums, as well as two reputable museums and two world-famous dance companies.
Westerly, Rhode Island
Despite having 400 miles of coastline in the Ocean State, Rhode Island's beaches are often overshadowed by those in Maine. Surprisingly, Taylor Swift, often mistakenly thought to be from the Deep South, owns a home in Westerly, her favorite staycation spot, seeking the serenity it offers. Despite being named Westerly, this beautiful and vibrant New England coastal destination is actually the southernmost town in Rhode Island, where “the beaches are just the beginning!"
Now add in a hopping downtown scene at its heart, and you've got your own slice of heaven in the charming town of Westerly. This real gem in the state is accessible with a delicious restaurant scene, local shopping and boutiques, trendy bars, and those beautiful, southernmost beaches with an applicable balmy atmosphere! Boasting swoon-worthy views along the three-mile-long Misquamicut Beach and the favored Watch Hill Beach, you can indulge in luxury at the Victoriana-style Ocean House Hotel, located right in Watch Hill.
The Takeaway
Comprising Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont, there's a New England vibe for every taste of quaintness. Low-key vibes prevail, from bustling fishing villages like Kennebunkport in Maine and Chatham in Massachusetts to the tranquil coastal towns of the Ocean State.
Newport, once an aquatic playground exclusively for the rich, is now accessible to all. Meanwhile, Westerly, renowned as one of the best shoreline destinations in southern New England, is favored by Taylor Swift as a perfect escape. These villages offer a step back to how life was in the old days, with weavings of modern attractions to unwind in style.
