9 Picture-Perfect Main Streets In New England
In Ridgefield, Connecticut, a British cannonball from 1777 is still lodged in the wall of a tavern on Main Street. In Woodstock, Vermont, a covered bridge sits a block from the town green. New England's best main streets are full of details like these, and many have changed little in two centuries. White steeples, brick storefronts, and old inns line their sidewalks. These nine are worth a slow walk with a camera.
Main Street, Damariscotta, Maine
Each October, the Damariscotta Pumpkinfest fills Main Street with giant decorated pumpkins, and its Pumpkin Regatta sends people paddling across the harbor in hollowed-out pumpkins. The street itself is a compact row of brick commercial buildings in this Maine town, most rebuilt after a fire in the 1840s, running down to the Damariscotta River.
Local bookshops, bakeries, and galleries fill the storefronts, and the river behind them is known for its oyster farms. Just upriver, the Whaleback Shell Midden State Historic Site preserves ancient oyster shell heaps left by Native people. The Skidompha Library and the restored Lincoln Theater give the street a lively year-round calendar.
Main Street, Hanover, New Hampshire
Hikers with backpacks are a common summer sight on Hanover's Main Street, where the Appalachian Trail runs right through town. Brick buildings, cafes, and bookstores line the New Hampshire college town's main drag along the edge of the Dartmouth College Green.
Lou's Restaurant and Bakery, a fixture since 1947, is the classic stop for breakfast and pastries. On the Green, the Hood Museum of Art offers free admission to a wide-ranging collection. The Hopkins Center for the Arts presents films, concerts, and theater through the academic year.
Central Street, Woodstock, Vermont
The Middle Covered Bridge crosses the Ottauquechee River just off the oval town green in Woodstock, where Central and Elm streets meet among Federal-style homes and churches. The F.H. Gillingham and Sons general store has been open since 1886 and still sells maple syrup, hardware, and nearly everything in between.
Marsh-Billings-Rockefeller National Historical Park, on the edge of town, preserves a historic mansion and forested trails. Across the road, Billings Farm and Museum is a working dairy farm with Jersey cows. In December, Wassail Weekend brings a parade of horses and carriages down the decorated streets.
Water Street, Exeter, New Hampshire
Exeter served as New Hampshire's capital during the American Revolution, a history told at the American Independence Museum. Water Street follows the Squamscott River through a downtown of brick storefronts, and the Swasey Pavilion bandstand on the town square hosts summer concerts.
Each July, the American Independence Festival fills downtown with reenactors, colonial music, and a reading of the Declaration of Independence. Phillips Exeter Academy, just up the street, is home to a striking library designed by architect Louis Kahn. Local bakeries, bookstores, and restaurants fill the storefronts in between.
Church Street, Lenox, Massachusetts
The Boston Symphony Orchestra spends its summers at Tanglewood, just outside Lenox in the Berkshires. In town, galleries, boutiques, and restaurants fill the historic buildings along Church Street. The short stretch comes alive in summer.
Author Edith Wharton's home, The Mount, offers tours of the house and gardens. Shakespeare and Company stages plays each summer, and Ventfort Hall adds a Gilded Age mansion to the town's grand architecture. At the top of the village stands the Church on the Hill, a white Congregational church.
Main Street, Northampton, Massachusetts
Since 1891, the Academy of Music Theatre has hosted films, concerts, and shows on Northampton's Main Street. Ornate brick and stone buildings from the 1800s line the street, and independent shops, restaurants, and cafes fill them.
Thornes Marketplace, in a converted department store, holds dozens of small shops. Just up the hill, Smith College has a historic botanic garden and the Lyman Conservatory, and the paved Norwottuck Rail Trail starts nearby. On warm evenings, street musicians and outdoor dining give this Massachusetts Main Street the busy feel of a much larger city.
Main Street, Chatham, Massachusetts
Seals swim near the Chatham Fish Pier while fishing boats unload their catch, a short drive from Chatham's Main Street. Shingled shops, inns, and the white-steepled First Congregational Church line the street at the elbow of Cape Cod.
On Friday evenings in summer, the town band plays free concerts in Kate Gould Park. Chatham Lighthouse overlooks the ocean at the end of Main Street, and the Chatham Railroad Museum preserves the town's old depot. Hanging flower baskets line the street, and in summer the sidewalks fill with families heading for ice cream and fudge.
Brown Street, Wickford, Rhode Island
Colonial homes from the 1700s line Brown Street and Main Street in Wickford on the way down to a small harbor filled with sailboats. The Rhode Island village, part of North Kingstown, holds one of the largest collections of 18th-century homes in New England.
The Old Narragansett Church, built in 1707, is one of the oldest Episcopal churches in the country. Each July, the Wickford Art Festival fills the village with artists. Smith's Castle, a historic plantation house, is just north of town. Small cafes and antique shops near the harbor make Wickford an easy place to spend a slow afternoon.
Main Street, Ridgefield, Connecticut
Changing exhibitions fill the Aldrich Contemporary Art Museum on Ridgefield's broad, tree-lined Main Street, where grand old homes give way to a small downtown of shops and restaurants. Nearby, the Keeler Tavern Museum still has a British cannonball from the 1777 Battle of Ridgefield lodged in its wall.
The Ridgefield Playhouse hosts concerts and films, and the town's parks and trails offer easy walks a few minutes from downtown. In December, the holiday stroll lights up Main Street with decorations and carolers.
Strolling New England
Each of these main streets grew up around something different. Damariscotta, Chatham, and Wickford face the water, and Chatham still runs on its fishing fleet. Hanover and Northampton take their character from their colleges, while Exeter and Ridgefield still carry the marks of the Revolution. Woodstock and Lenox drew wealthy families in the 1800s and early 1900s, and the grand homes and estates they left behind still shape both streets.
