10 Best Downtowns In New England
New England, consisting of six different states - Maine, New Hampshire, Vermont, Massachusetts, Connecticut, Rhode Island - and replete with mountains, forests, and valleys, can be a tranquil, majestic place. Yet, there are many towns scattered across New England as well, and most of these towns have exceptionally thriving downtowns. From picturesque Kennebunkport, Maine, and its waterfront downtown to the scenic town of Ridgefield in Connecticut and its mile-long downtown, the ten towns below promise more than just token museums and art galleries. From annual festivals to unique outlet stores to delectable menu items served in local restaurants, these ten towns in New England have some of the best downtowns in the United States.
Kennebunkport, Maine
The coastal town of Kennebunkport, situated about 25 miles northeast of Portland, has one of the best downtowns in Maine. Dock Square, consisting of several streets, is overflowing with thriving shops, like Sea Love Candles and Daytrip Society, as well as several great dining choices. The Hurricane Restaurant, right on Dock Square, serves everything from tasty racks of lamb to delicious stuffed lobsters.
Several annual festivals are held in downtown Kennebunkport, including the Christmas Prelude in the first half of December. Along with lighting the town square Christmas tree, caroling with the community at the monastery, and catching sight of some awesome fireworks, the whole event ends when Santa Claus arrives on the back of a lobster boat.
Portsmouth, New Hampshire
Thirty miles southwest of Kennebunkport, the town of Portsmouth has its own thriving downtown area. Accurately named Market Square, the downtown area has several great restaurants, like Portsmouth Gas Light and Jumpin’ Jays Fish Cafe. Whether you want fine dining or a casual spot to grab a bite, anyone can appreciate freshly caught seafood or that perfectly cooked steak in downtown Portsmouth.
Several unique outlet stores and art galleries are also located in Market Square. Macro Polo and A Pleasant Shoppe both have an abundance of fabulous gifts for the people back home. Jimmy’s Jazz & Blues Club is also situated in downtown Portsmouth, waiting to entertain you with some of the most enlightening musical performances in New Hampshire.
Middlebury, Vermont
Approximately 35 miles south of Burlington, along the eastern border of northern New York state, downtown Middlebury, Vermont, is an ideal place to visit. From the annual festivities like Festival on the Green, with performances by outstanding local musicians, to outlet shops like Adagio Chocolates and Autumn Gold, the downtown area in Middlebury has something for everyone.
There are also several excellent dining options in downtown Middlebury. Fire & Ice has private dining rooms and even a fireplace to take away the chill, while Mr. Up’s has its own private riverside deck on which to dine. And, if you are in Middlebury during autumn, the Middlebury Car Show & Fall Festival takes place every year in October, offering a car show with 75 different classic cars and trucks and a multitude of food vendors.
Falmouth, Massachusetts
Just north of Martha’s Vineyard and Vineyard Sound, the quaint town of Falmouth has a superb downtown area. The Historic Village Green District offers everything from Colonial-Age buildings like the Conant House, first built in 1730, to Museums on the Green, with exhibits featuring the American Revolutionary War and artifacts relating to the maritime history of the area.
Downtown Falmouth is also home to several awesome seafood restaurants, like Pier 37 Boathouse and Quarterdeck. Both offer a steak and seafood surf-n-turf. Plus, during the month of September at the Cape Cod Fairgrounds, the Cape Cod Brew Fest presents over 150 samples of microbrews from 50 different microbreweries, as well as some phenomenal music and a multitude of food and craft vendors.
Bristol, Rhode Island
The picturesque coastal town of Bristol, approximately twenty minutes south of Providence, Rhode Island, has a thriving downtown and a happening coastal region. Along with Blithewold Manor, Gardens, & Arboretum, which offers late 19th-century architecture, phenomenal flora, and even a great wedding venue, downtown Bristol is overflowing with some excellent restaurants, like DeWolf Tavern and the Beach House.
Another great attribute of downtown Bristol is the State Street Harvest Fair, held at the end of September every year. It offers over seventy different arts and crafts vendors and a plethora of varying cuisine choices. They also have some excellent local musicians, some delicious locally grown produce, and the chance to mingle with locals as well as people from all over the state.
Camden, Maine
Known best for its picturesque harbor, dotted with sailboats, yachts, dinghies, and windjammers, and its historic inns, like Norumbega, set inside a 19th-century stone castle, and 20th-century Whitehall Inn, downtown Camden is the perfect spot for a vacation in Maine. It is also especially unique, as it has some of the most beautiful boutique shops, like House of Logan and Leonard’s.
From the High Street Historic District, displaying over fifty different 18th, 19th, and 20th century buildings, and Harbor Park, first designed in the 1930s, the downtown area of Camden has some phenomenal historic value. Chestnut Street Historic District, close to Village Green, has even more architectural wonders and some of the best views of panoramic Penobscot Bay.
North Conway, New Hampshire
Beginning at the L.L.Bean Factory Outlet and ending near the Kahuna Laguna Indoor Water Park, the town of North Conway is home to one of the best downtowns in all of New Hampshire. Whether you are looking for a popular outlet store like Yankee Candle or Banana Republic, or a hometown shop like Zeb’s General Store, downtown North Conway is the place for everyone.
Downtown North Conway is also home to some phenomenal restaurants and lodging choices. Wicked Fresh Craft Burgers is just north of Settler’s Green, and Foxridge Resort sits across from Sea Dog Brewing Company. Several awesome festivals also take place in downtown North Conway each year. The Busker Festival occurs every October, featuring a variety of bluegrass, jazz, and rock ' n ' roll music performed by some phenomenal musicians throughout Settler’s Green.
Burlington, Vermont
Burlington, the largest town in Vermont, though it still has fewer than fifty thousand residents, has a phenomenal downtown. From Main Street, leading visitors past City Hall Park to Battery Park and Lake Champlain, to Church Street, a pedestrian-only street and home to Church Street Marketplace, boasting over a hundred shops and diners, downtown Burlington is an awe-inspiring experience, no matter who you are.
Along with Church Street Marketplace and eateries like Leunig’s Bistro, downtown Burlington also has some fantastic festivals and events. Ri Ra Irish Pub presents several weekly events, like MixTape Mondays and Trivia Night every Wednesday. Plus, each year in October, Church Street presents a Howl’ween Dog Costume Contest and a Halloween Bike Ride costume contest.
Bar Harbor, Maine
Best known as a gateway to Acadia National Park, Bar Harbor also boasts one of Maine’s most inviting downtowns. Stretching from the YMCA Ball Park along Main Street to the Village Green and down to Agamont Park on the waterfront, the district is a lively mix of shops, restaurants, and cultural attractions. Visitors can browse the Eden Farmers Market, pick up gifts at the whimsical Cool As A Moose shop, or indulge in hand-made fudge and chocolates at Ben & Bill’s Chocolate Emporium, a local favorite.
The Village Green serves as a centerpiece of community life, with weekly summer concerts and seasonal festivals that give downtown a welcoming energy. Dining options are plentiful, ranging from casual taverns to atmospheric pubs like Paddy’s Irish Pub, which blends nostalgia with hearty fare. Just a short walk away, Agamont Park provides stunning views of Frenchman Bay, making it the perfect spot to watch the sunrise or relax after a day in Acadia.
Ridgefield, Connecticut
The picturesque town of Ridgefield, situated only a few miles east of the state of New York and about an hour north of New York City, has a downtown area that is well worth visiting. Whether you're looking for peaceful ambiance in Ballard Park, quaint shops like Books on the Common on Main Street, or delectable farm-to-table eateries like Bailey’s Backyard, downtown Ridgefield has a plethora of awesome new experiences for everyone.
There are also a variety of festivals that take place in downtown Ridgefield, like the Ridgefield Arts Festival, held every year in Ballard Park during June with 100 different arts and crafts vendors and plenty of food options. There is also the Ridgefield Holiday Stroll to check out, with DJs playing the holiday hits, horse-drawn carriages, and, of course, the local stores staying open even later for that special holiday shopping.
Finishing Thoughts
Whether you find yourself in downtown Burlington, beside Lake Champlain, or in downtown Bar Harbor, along the rugged coast of Maine, the downtown areas of the ten towns above, scattered across the northeastern section of the United States, are some of the best to be found anywhere. Each one blends historic charm with lively festivals, unique shops, and inviting eateries. Exploring them offers a true glimpse into the culture and spirit of New England, making every visit both memorable and rewarding.
