10 Charming Main Streetscapes In New England
The pretty main streets of New England are the vibrant hearts of these historical towns, from the rocky coastal towns of Maine to the mountains in Vermont. The historic town centers host festivals throughout the year, from celebrating Christmas in the winter markets of Nantucket to Irish heritage around St. Patrick's Day in Mystic.
These main streets serve their communities, and local businesses thrive. Find locally produced artwork in Bath, or locally brewed beer in Bennington. If it matters to the community, these main streets have it. All year long, these pretty main streets support their communities.
Damariscotta, Maine
Oyster shell dumps piled thirty feet deep line river banks in Damariscotta, Maine. The shell middens, as the piles are called, were created by Native Americans between 1,000 and 2,200 years ago, though in the 19th century many of the piles were mined to make chicken feed. Today, on Main Street, the Whaleback Shell Midden Historic Site includes a half mile hiking trail loop where visitors can see the remains of the shell heaps.
Oysters remain a big part of Damariscotta's local economy. Continue down the pretty Main Street to the waterfront along the Damariscotta River where Damariscotta River Cruises offers narrated boat tours of the oyster farms, scenic foliage, and migratory birds like eagles and ospreys. Main Street restaurants like River House serve up local oysters with a pomegranate-flavored mignonette.
Main Street here hosts annual festivals, like the Damariscotta Pumpkinfest and Regatta featuring a parade down Main Street and a Pumpkin drop. The 1,000 pound pumpkins splatter on the ground when they are dropped from a crane that hoists them 160 feet into the air.
Over Thanksgiving weekend, Main Street lights up with more than 70 Christmas trees as part of the annual Villages of Light Festival, extending into New Castle across the river. The event is also a great opportunity to visit the local shops along the Main Street, like Wildings featuring a curated selection of home decor, candles, and handmade pillows.
Bath, Maine
The Gettysburg Tree in front of the Old Customs House in Bath, Maine descends from a honey locust sapling grown from a tree that witnessed Abraham Lincoln deliver the Gettysburg Address, in Gettysburg, Pennsylvania in 1863. The tree honors the memory of former Customs House trustee Edward True II. Today, the tree stands at the entrance to the pretty main Front Street in the central business district.
Locally owned shops line Front Street, like Maine Street Mercantile featuring a rotating selection of artwork from local artists, vintage furniture and objects, and consignment pieces. The Corner Bookshop has a large selection of pre-owned books as well as a curated selection from local authors. On the third Friday of each month, from June through October, the Bath Art Walks showcase works at 16 galleries along Front and Centre Streets.
In the summer, Bath hosts their annual Heritage Days, a multi-day festival with live music performances, July 4th Fireworks, a carnival along the waterfront, and a car show takes over Front Street.
Each winter, Bath Winterfest heads downtown with winter games like a Yeti relay, disc golf, and hockey tournament, all leading up to the annual Lantern Parade featuring a local Yeti.
Plymouth, New Hampshire
Babe Ruth traveled to Plymouth, New Hampshire, in 1916 so that he and the other Red Sox players could be fitted for baseball gloves. The local Draper & Maynard Co. had grown into a hugely important manufacturer of gloves, baseball bats, and other pieces of equipment. During the visit, Ruth even stitched a baseball. The moment, captured on film, hangs in the historic factory building that sits on Main Street in Plymouth.
Home to Plymouth State University, the campus borders the charming downtown along the Main Street. Located right on Main Street, the university's Silver Center for the Arts serves as central New Hampshire's primary performing arts venue hosting a variety of shows including comedy, lectures, recitals, and live music.
The center also hosts the annual New Hampshire Music Festival featuring orchestral and chamber music with a Music in the Mountains program, that brings live music throughout communities in the White Mountains, including venues like Cafe Monte Alto on Main Street in Plymouth.
Just down Main Street, the Flying Monkey hosts films and live shows. Originally opened in the 1920s as a vaudeville theater, it was restored in 2010 and today serves as a community hub. The theater shows classics like the Rocky Horror Picture Show as well as foreign films and children's movies.
Claremont, New Hampshire
The power generated on the Sugar River helped drive the industrial revolution in Claremont, New Hampshire. Mills like the Sullivan Machine Company, built in 1868, lined Main Street. Today, the mills are closed, but the historic building has become the Claremont MakerSpace serving as a hub with membership-based access to classes, tools, machinery, and creative community. The organization also spearheads the Claremont Art Walk featuring 14 stops at galleries in the downtown.
The pretty Main Street leads into Opera House Square where the Claremont Opera House has stood since 1897. Restored in the 1980s, the opera house today serves as a center of live entertainment including touring comedians, musical performances, and holiday events like How the Grinch Stole Christmas Ballet.
Next door, the West Claremont Center for Music and The Arts supports local events throughout the community, including the Summer Concert Series in Broad Street Park, just across the street.
Small shops line Opera House Square like Violet's Book Exchange offering used books and store credit for trade-ins, or Claremont Spice and Dry Goods with local and international spices, tea, dried peppers, and coffee.
Bennington, VermontThe Bennington Battle Monument in Bennington, Vermont.
At the center of Bennington, Vermont, the "Four Corners" intersection leads everywhere in town, and a public art piece painted on the street includes a North Star Compass. The compass dates to 2017 and features piano keys along the border. More recently, a celebration of the 250th anniversary of the United States was added to the now iconic street art.
Heading west on Main Street from the four corners intersection leads to the Bennington Theater where live entertainment can be found year round, including Broadway-style theater shows, youth community theater, and live music. The theater hosts the Vermont Film and Folklore Festival, an annual celebration of storytelling. The multi-day festival includes documentary shorts, folktale stories, and Vermont-made films.
The annual Bennington Mayfest Arts and Crafts Festival takes over Main Street each spring showcasing the work of artists and artisans from southwestern Vermont. The family-friendly event includes live music and more than 130 vendors featuring handmade items like pottery, woodworking, and specialty gifts. The fair extends from Four Corners along Main Street.
Heading east on the pretty Main Street leads to local shops, restaurants, and bars, like the Madison Brewing Company Pub and Restaurant. The brewing company has a selection of local beers on tap and casual pub food from the kitchen.
Mystic, Connecticut
The counterweights on the Mystic River Bascule Bridge in Mystic, Connecticut weigh 230 tons, made from concrete. The counterweights help the bridge open more than 2,200 times each year, disrupting traffic on Main Street.
In season, the bridge opens once an hour, but don't expect it to open during the annual Mystic Irish Parade in March. The celebration of Irish heritage includes over 2,000 participants marching a route from the Seaport Museum to the Mystic Museum of Art on a route that carries the parade directly across the bridge. The parade includes more than 100 units of bagpipes, bands, vintage vehicles, and heritage organizations.
In November, expect the Main Street bridge to be in the up position for the Mystic Holiday Light Boat Parade. The illuminated vessels, lit up with holiday lights, sail down the river to be judged in categories like "Best Dressed Vessel" and "Most Charismatic Crew." The boats pass by Mystic River Park, a waterfront greenspace and walkway that can be easily accessed from Main Street. The park also hosts Summer Sounds, a free concert series on Tuesdays through the summer featuring local musicians.
Wickford, Rhode Island
One of the oldest colonial-era villages that remains intact today, Wickford, Rhode Island's historic downtown remains frozen in time. Built along a protected cove off Narragansett Bay, historic buildings line Main Street in this bayside port town. Small shops keep these historic buildings alive, like quilting supply store The Sew-Op and the antique furniture shop, My Paris Apartment. Each October, Main Street hosts the annual Horribles Parade, a celebration of spooky Halloween costumes followed by Trick-or-Treating at these local storefronts.
In the summer, the annual Wickford Art Festival takes place at Wilson Park on Main Street. Hosted by the Wickford Art Association, the festival features both 2D and 3D artwork, a juried artshow, and art vendors.
Wickford is often considered the inspiration for John Updike's The Witches of Eastwick. Each October, the town also hosts an annual Witches Paddle in the harbor where dozens of costumed witches paddle around in kayaks, rowboats and paddle boards to raise money for the North Kingstown Food Pantry.
Nantucket, Massachusetts
The cobblestone pavers in Nantucket, Massachusetts makes this Main Street one of the prettiest in New England. Nantucket Island is a popular summer destination, but the Main Street also comes alive in December during Christmas Stroll Weekend.
The Town Crier announces Santa's arrival when his boat docks at the Straight Wharf at the end of Main Street. All day long, Victorian carolers sing, and artisan vendors set up shop in the parking lot alongside Main Street.
The small shops along Main Street also offer a great place to find holiday gifts, from national chains like Vineyard Vines and Ralph Lauren, to local brands like Four Winds Gifts stocked with American made arts and crafts. For an edible gift, check out Aunt Leah's Fudge featuring taffy, chocolate covered cranberries, and handcrafted chocolate confectionery.
After a day of shopping, stop in at the Gaslight at the corner of Union and Main where an intimate performance space hosts live music and karaoke with an Asian-inspired food menu. The Gaslight also hosts an annual New Year's Eve Party with live music.
Provincetown, Massachusetts
Many of the buildings along Commercial Street in Provincetown, Massachusetts started off at Long Point before they were floated across the harbor. Long Point at the tip of Cape Cod was once a small fishing village, but by the 1850s, the combination of declining fish yields and isolation led the families to float their houses to present-day Provincetown. During this period, the pretty main Commercial Street began to take shape.
In 1860, the Center Methodist Episcopal Church was built at the center of the newly formed community. Today, the church serves as the Provincetown Public Library. Inside, visitors will find plenty of books, but the real attraction here is the half scale model of the schooner Rose Dorothea. Even as a scale model, the little boat fills the floor. The top floor of the library also offers sweeping views of the harbor and pretty Commercial Street.
A few blocks down Commercial Street, the Bob Gasoi Memorial Art Alley is a narrow public street filled with sculptures and paintings. A combination of murals and metal found art sculptures, the curious art alley is a unique, and pretty addition to Commercial Street.
At the center of town, the annual Lobster Pot Tree Lighting fills Commercial Street with holiday cheer. The Christmas Tree, constructed out of lobster traps, rises in the center of Lopes Square in honor of the town's lobsterman. The community sings holiday songs and just after dark, lights up the tree. And on New Year's Eve, the First Light Celebration fills Commercial Street with merriment before a drone-show lights up the harbor.
Charming Main Streets Make Communities Thrive
Halloween parades in Wickford Village, Pumpkin festivals in Damariscotta, and Santa arriving by boat in Nantucket bring these historic main streets to life. These pretty places are the center of their communities where people come together. These main streets are places to be entertained, where people can enjoy live music, like in Plymouth at the New Hampshire Music Festival or films at Bennington's Film and Folklore Festival. These streets are more than just roadways. They create community by being places people want to spend time.
