8 Picture-Perfect Main Streets In New England
When it comes to photo-worthy main streets, New England is hard to beat. Many towns date back to America's early days and still retain much of their early American charm with stately stone buildings, colorful wood-paneled shops, and brick-lined sidewalks. Take, for example, Stockbridge, where you can enjoy a fine-dining experience at an 18th-century inn, or the Market Square in Newburyport, where historic storefronts house stores selling everything from classy European fashion to gourmet food. It is that extra care to honor their roots that sets these 8 towns apart, and why their Main Streets will have you taking picture after picture.
Mystic, Connecticut
Located along the Mystic River, the small village of Mystic, Connecticut, combines waterfront views with a highly walkable downtown. Along Main Street, you’ll find plenty of charming historic architecture, such as the Whaler’s Inn, a boutique hotel with 6 buildings dating as far back as the 1800s. But the local shops and galleries are what really give Main Street its charm, with their elegant two-story facades, bright colors, and large window displays. This is where you’ll find the iconic Mystic Pizza (the namesake of the 1988 movie hit), which is worth a stop for a slice and a few photos. At the heart of Main Street, the Bascule Bridge is also a popular stop to see the counterweighted drawbridge open and close throughout the day.
Stockbridge, Massachusetts
Founded in 1734, Stockbridge has a rich history that’s easily seen in the historic homes and buildings around town. But Main Street, the inspiration for Norman Rockwell’s Stockbridge Main Street at Christmas and one of the most photographed Main Streets in America, is easily the best place to start your exploration. The shops and homes along Main Street bring diverse Victorian, Federal, and Colonial architectural styles together into one beautiful conglomeration. The historic Red Lion Inn is always a good stop, too, not only for its eye-catching 18th-century architecture, but also for an elegant meal in the Inn’s Main Dining Room. Continue your exploration with a stroll through Laurel Hill Park, a lovely forested park along Main Street that’s listed on the National Register of Historic Places.
Littleton, New Hampshire
Tucked away by the White Mountains and along the banks of the Ammonoosuc River, Littleton, New Hampshire’s geographical location already gives it plenty of picturesque appeal. But its Main Street, which has been a finalist for the Great American Main Street Award two times, is definitely worth a long stroll. You can easily spend hours meandering through the classic brick buildings (many of which have impressive facades), browsing toys, antiques, jewelry, and more. Here, you’ll find Chutters, a candy store that holds the Guinness World Record for the longest continuous candy counter. Close by, a life-size statue of the classic book character, Pollyanna, smiles over the town in honor of author Eleanor Hodgman Porter, who was born in Littleton. The historic Littleton Opera House is also a well-visited landmark, rising over Main Street with a four-story octagonal tower.
Stowe, Vermont
Another mountain gem, Stowe, Vermont, pairs a historic downtown village scene with spectacular mountain views, making its Main Street beautiful from every angle. Stowe's Main Street sweeps through the historic center, lined with a colorful array of 19th-century homes, small brick and painted wood shops, and the iconic Stowe Community Church, complete with a white steeple. Stop by The Country Store on Main for elevated finds, ranging from home decor to clothing. The Butler's Pantry Breakfast and Dinner, located in a cozy brick home, is a popular choice for a hearty meal. But there's plenty more to explore here, from clothing boutiques and chocolate shops to the Vermont Ski and Snowboard Museum.
Camden, Maine
Peacefully situated on West Penobscot Bay, Camden, Maine, has plenty of quintessential New England charm, both natural and historic. But Main Street is a fantastic place to start before expanding into the harbor and the residential areas, which are known for their beautiful homes with charming front porches. Walking down Main Street, you’ll find a gorgeous mix of color and styles: tall brick businesses nestled up against wood-paneled buildings, classic brick and brightly-painted hues, and overflowing flower displays. There’s an eclectic mix of shops and eateries here, too. You can shop for farm-fresh lavender and lavender-themed products at the Glendarragh Farm Lavender and hand-tooled classy leather goods at The Leather Bench before tucking into a fresh deli sandwich and locally made cupcakes at Camden Deli. Don’t miss a slight detour into the adjoining Harbor Park for beautiful views of Camden Harbor.
Essex, Connecticut
Named as the “Perfect Small American Town” in 1,000 Places to See Before You Die, much of Essex’s charm comes directly from its Main Street in the historic Essex Village (not to be confused with Main Street in Essex proper). Lined with beautiful maritime buildings, Main Street weaves through Essex Village, branching into north and south offshoots, and ultimately ending at the Connecticut River. As you meander Main Street, you’ll see lovely homes bordered with white fences, stroll down tree-lined sidewalks, and pop into large-windowed shops brimming with charm. There’s a mix of 18th and 19th-century architecture throughout the area, weaving seamlessly into one scenic village. When you’re done browsing, be sure to stop by the Connecticut River Museum for some local shipbuilding history and The Griswold Inn for a tasty meal (or stay) in one of America’s oldest continuously operated inns.
Newburyport, Massachusetts
Historic Newburyport holds one of the most eye-catching main streets in New England, thanks to its stately brick row houses, brick sidewalks, and cobblestone accents. The main street in Newburyport is State Street, which leads directly to the historic Market Square shopping district and ends just a short walk from the waterfront. State Street is a local shopper’s paradise, with plenty of options for every interest: gourmet food, baby clothes, jewelry, European fashion, and more. The stately brick buildings will likely hold your attention just as much as the stores inside. The Nauti Pearl is a popular store on this street known for its fashionable women's clothing, while The Coffee Factory is a great place to enjoy a good coffee and sandwiches. Market Square (once a commercial hub for merchants and traders) contains even more boutique shops surrounding a peaceful brick plaza.
Bar Harbor, Maine
For those who prefer a stunning coastal town with a bit of extra flair, Bar Harbor, Maine, has a vibrant, historic Main Street that’s best explored on foot. Tree-lined sidewalks lead past stately clapboard buildings with pitched roofs and colorful trim, with a view that extends to the water. When you’ve had your fill of shopping, check out the Main Street locations of the self-guided Museum in the Streets tour. Then, take in the local nature with a visit to Village Green, a lush town square with multiple fountains and a War Memorial. Agamont Park is another well-loved spot at the north end of Main Street, featuring lots of green space and sweeping ocean views.
Fill Up Your Camera Roll At These Picture-Perfect Main Streets
Mountain views, maritime vibes, and historic architecture: you’ll find it all when you explore these 8 beautiful towns scattered across New England. Each one has its own unique atmosphere: some are bustling and vibrant, while others are peaceful and understated. But they share a common pride in preserving their history. So, while there are many lovely towns across New England, these 8 stand out for their picture-perfect main streets that feel like a little step back in time.
