9 New Hampshire Towns With Unforgettable Main Streets

Small towns appearing pulled directly from a postcard have a certain undeniable charm. The old buildings, eclectic shops, docks, and local restaurants create an atmosphere far removed from big city life, thus leading to a relaxing vacation. New Hampshire, one of the original 13 US states, teems with postcard-perfect small towns.

Part of the New England region, New Hampshire is surrounded by Maine, Massachusetts, Vermont, and the Canadian province of Quebec. New Hampshire’s gorgeous and diverse landscape showcases mountains, rivers, and flourishing forests. While there is much to do throughout the state, sometimes, on vacation, you want to explore the downtown areas where you may not need to drive, and walking or biking is possible.

Pull out your suitcase and get ready to uncover nine small New Hampshire towns with some of the best downtown areas.

Portsmouth

Positioned in southeastern New Hampshire is the city of Portsmouth, a breathtaking coastal gem overflowing with history and heritage. Portsmouth is the state’s oldest settlement, first capital, and only seaport. It sits across from the Piscataqua River from Kittery, Maine, and is the birthplace of New Hampshire’s first newspaper, the New Hampshire Gazette, and home to the Portsmouth Naval Shipyard.

Amidst Portsmouth’s many downtown restaurants and shops are historical landmarks such as the Moffatt-Ladd House and Garden and the Portsmouth Athenæum. Since 1912, the Moffatt-Ladd House has been a national landmark, inviting visitors to tour its 1764 architecture and surrounding stunning garden, where you can participate in High Tea at the Harbour View Garden area. The Portsmouth Athenæum is an expansive red brick facade membership library, a relic from when there were once hundreds of membership libraries throughout the US. The library maintains tradition by housing over 40,000 volumes, manuscripts, photographs, and objects.

Grab a bite to eat at Portsmouth Gas Light Co. The restaurant, music scene, and nightclub are inside the former 1837 building that housed Portsmouth’s first utility services, the Portsmouth Gas Light Co. If you want entertainment in a more subdued setting, check out Jimmy’s Jazz and Blues Club. Bringing together the community to listen to jazz and blues artists in world-class listening rooms, Jimmy’s is for music lovers who enjoy the ultimate sensory experience.

Wolfeboro

Surrounded by mountains and lush forests is a classic New England town, Wolfeboro, New Hampshire. Known as America’s Oldest Summer Resort, Wolfeboro is an excellent small town for individuals looking to enjoy stunning views and fun activities.

Amongst Wolfeboro’s downtown area are several historical buildings to feast your eyes upon. Learn about the city’s oldest buildings through a Downtown Historic Walking Tour. Some spots along the route include the 1872 Wolfeboro Railroad Station and the 1853 Black’s Paper Store. Locals enjoy cooling off on warm days with a scoop or two from Bailey’s Bubble. The summer seasonal destination is for those who enjoy classic options like ice cream floats, sundaes, and even hand-packed pints. You can take your ice cream to go and head over to the Wolfeboro Town Docks and watch as the boats drift by on the Wolfeboro Bay.

Dover

History lovers looking for a small-town getaway should head to Dover, New Hampshire, the oldest permanent settlement in the state. Part of Strafford County, Dover, established in 1623, is rich with history; much of it is evident in the town’s architecture.

The downtown area features some of Dover’s oldest structures. Walk along the streets, and you will find buildings displaying architecture from several eras with historic markers highlighting the past. One such building is the Woodman Museum on Central Avenue, which features the Woodman House, built in 1818, the former home of Captain William Palmer. Another must-see building on this street is the First Parish Church. The church was built in 1634 and is one of the oldest Parishes in the country.

Dover is a family-friendly town with activities perfect for children. On Washington Street, the Children’s Museum of New Hampshire offers two floors of custom-created interactive exhibits for kids of all ages. Children can excavate dinosaur fossils, play music, or navigate a submarine. Nearby, you can get an up-close view of the Cocheco River. Take the Riverwalk from downtown to witness the mighty 33-foot falls.

Littleton

Littleton, New Hampshire, evokes the essence of a quintessential cozy mountain town. The city provides a welcoming small-town feel with its New England-style brick architecture and walkable Main Street. Littleton sits just north of the White Mountains, beside the banks of the Ammonoosuc River.

In the heart of Littleton's downtown is an over 100-year-old Opera house. Littleton Opera House hosts live performances annually, including concerts, plays, and comedy acts. One of the town's most notable attractions is Chutters, a candy store home to the Guinness World Record holder for the longest candy counter of 112 feet. Since the 1800s, Chutters' vibrant pink and purple storefront has beckoned travelers and locals to enjoy its confectionery offerings. Another draw to the town of Littleton is the Pollyanna statue. The bronze sculpture is a tribute to Eleanor H. Porter, the brains behind one of the most optimistic fictional characters, Pollyanna. No visit to a small town is complete without visiting the local small shops. Family-owned White Mountains Canning Co. sells over 100 locally made jams, jellies, pickles, and other canned goods so you can bring home a taste of Littleton.

Plymouth

Lying in central New Hampshire, on the Pemigewasset River, is Plymouth, a small town established in 1763. The charming downtown of Plymouth offers views of historical buildings with brick facades and quaint spots to grab a bite, and it is home to Plymouth State University.

On Main Street is Chase Street Market, a hub for locals, students, and visitors, beckoning individuals with eateries and coffee shops, such as Cafe Monte Alto. One can find single-origin roasts and classic offerings like lattes and cold brew here. Nearby, serving up breakfast and lunch specials daily, is The Main Street Station. Local favorites include Raspberry Cream Cheese Stuffed French Toast and Eggs Benedict. In the downtown area, visitors can find Plymouth State University. The campus has multiple historical buildings, including the former Draper and Maynard Sporting Goods Factory. The 1890s building produced sporting equipment like the padded glove for professional baseball to reduce injuries. Another historical site on the university grounds is the 1891 Rounds Hall, which was once a boarding house and later a library and classrooms. Since 1975, a peculiar tradition has remained with Rounds Hall, where just before Halloween, two pumpkins appeared on the spires above the clocks of Rounds Hall.

Hanover

Hanover, New Hampshire, is a collegiate town in western New Hampshire, home to Dartmouth College. The city’s walkable downtown offers eclectic shops, inviting restaurants, and vibrant charm.

While in Hanover, consider shopping for your next read on South Main Street at Still North Books and Bar, an independent bookstore, bar, and cafe. The shop provides a curated selection of literature and a menu of light bites, craft beer, wine, and caffeinated confections. If second-hand shopping for books is more your speed, head north a few paces and you will end up at Left Bank Books. Community-supported through donations, Left Bank Books has been a community staple since 1999. Next door, you can grab a coffee and pastry from Dirt Cowboy Coffee. The coffee shop serves freshly roasted and individually brewed coffees and, for 15 years, has been voted the Best Gourmet Coffee Shop in the region. Check out Nugget Theaters south on South Main Street for a little entertainment and exposure to local history. Since 1916, the small local theater with only four screens has entertained audiences with shows in a comfortable and charming setting.

Keene

In southwestern New Hampshire is the city of Keene, a city incorporated as a town in 1753 after being named for Sir Benjamin Keene, an English minister for Spain. Keene is located in Cheshire County, on the Ashuelot River, and is rich in culture and activities for people of all ages.

Along the downtown area of Keene, you can find an array of local businesses selling unique souvenirs and goods. Hannah Grime’s Marketplace on Main Street features touristy favorites, such as Keene t-shirts and magnets, as well as more distinctive wares to bring home after your travels, like ceramics and blown glass produced locally. For some local history, the Wyman Tavern is also on Main Street. The 1762 building depicts the Georgian architectural style and offers tours to the public. Stroll around downtown, and you can find an array of murals. Take the Walldog Mural Walking Tour to cover all 16 stops and view the murals that, on average, span across 350 square feet, depicting historical figures, the railroad that made the town into what it is today, and more. In the center of downtown Keene is Central Square, the perfect peaceful spot to pause from all the walking and enjoy community events. The Square houses an endearing gazebo, a fountain, and the Civil War Soldier’s Monument.

North Conway

In the Mount Washington Valley is North Conway, New Hampshire, a small New England town known to be one of the best ski towns in the US, providing skiers and snowboarders with seven alpine resorts with over 300 trails to explore. While North Conway is beloved for its outdoor adventures, it also features an active downtown area, North Conway Village, with fun ventures that do not require hitting the slopes.

Climb aboard the Conway Scenic Railroad for a family-friendly escapade to Conway, Bartlett, or the mountains and Crawford Notch. The old-fashioned train ride offers heritage train rides or scenic railroad excursions. To continue with the theme of yesteryear, step into Zeb’s General Store, a shop embodying the whimsy of general stores from decades ago. The store features displays on antique store fixtures, an old-fashioned candy counter, New England-made specialty foods, and nostalgic items seemingly pulled directly from childhood memories. Of course, dining on local cuisine is a must with any trip. Table and Tonic provides delectable breakfast items, sandwiches, soups, and more made from local produce, dairy, and humanely raised meats.

Exeter

Founded in 1638, Exeter, New Hampshire, is a quaint small town with a downtown district full of historic sites. In its early beginnings, Exeter was a commonwealth independent of the English colonies. The town is in southeastern New Hampshire, on the Exeter River at the falls of the Squamscott River.

One of the city’s most iconic and photographed spots is the Exeter Town Hall, built in 1855, where public meetings and events occur. On top of the cupola is the Statue of Lady Justice, a replica of the original statue destroyed by a hurricane in the early 1990s. The Powder House, constructed in 1771, is another of Exeter’s historic features. Located at Duck Point, the building stored materials for the War of 1812.

Wander over to the Big Bean for unique gourmet meals available seven days a week. From burritos for breakfast to cocktails with dinner, the restaurant serves meals using seasonal produce, homemade bread, and provisions from local farms. Take lunch to go and head over to Founders Park. The city created the area in 1988 to commemorate the 350th anniversary of Exeter. It is a perfect spot to enjoy the Squamscott River views, people-watch, and dine on something local.

New Hampshire is a beautiful state to visit, and with so many things to do, it will make you want to keep coming back. People who love old buildings are in luck with the First Parish Church in Dover and especially with the Downtown Historic Walking Tour in Wolfeboro. Foodies have so many options to indulge in delicious foods like Raspberry Cream Cheese Stuffed French Toast from The Main Street Station in Plymouth or the burritos from the Big Bean in Exeter. Book lovers can travel to Hanover to shop at the used and new bookstores or the historical Portsmouth Athenæum in Portsmouth. Unique, family-friendly fun awaits North Conway with the Conway Scenic Railroad and the 112-foot candy counter at Chutters in Littleton. Keene provides a blend of history and local charm. Add these nine New Hampshire towns with unforgettable main streets to your bucket list for a guaranteed fun time.