The Main Street lined with historic buildings in Wolfeboro, New Hampshire.

6 Cutest Small Towns In New Hampshire To Visit In 2024

In the heart of New England, New Hampshire entices visitors with its blend of artistic flair and outdoor splendor. Renowned for its picturesque landscapes, including the majestic White Mountains and tranquil lakeshores, the Granite State is a haven for outdoor enthusiasts. But beyond its natural beauty, New Hampshire boasts a vibrant arts scene, with charming towns like Peterborough, Newmarket, Littleton, and Wolfeboro. From scenic hiking trails in Gilford to bustling art galleries in Plymouth, New Hampshire’s rich cultural heritage amidst stunning natural surroundings is waiting to be discovered in 2024.


Aerial view of buildings in Wolfeboro, New Hampshire.
Aerial view of Main Street and the coast of Lake Winnipesaukee in Wolfeboro, New Hampshire.

Often referred to as “The Oldest Summer Resort in America,” visitors to Wolfeboro might feel like they’ve stepped back in time to a place where nothing has changed. With a Norman Rockwell-esque appeal, the town traces its history back to 1759. Visitors can stroll along the town's waterfront promenade, Wolfeboro Bay, and admire views of Lake Winnipesaukee and the surrounding mountains. Cute shops line downtown Wolfeboro’s Main Street, like Black Paper Store & Gift Shop, which first opened its doors in 1867 as “Black’s Paper Store” and has morphed into a one-stop-shop for just about everything—books, art supplies, snacks, and souvenirs. The historic Wolfe’s Tavern has been a place to “eat, drink, gather” for over 130 years.

Don’t be surprised to spot brightly painted pianos in and around town during the summer of 2024. The pianos are part of the Street Piano Project, a visible and hands-on way to engage the community to share in the joy of music, and an initiative of Great Waters that sponsors the annual Great Waters Music Festival held in Wolfeboro and nearby Moultonborough. After an outdoor concert in Wolfeboro, outdoor enthusiasts can enjoy activities like boating, fishing, and hiking in nearby parks, such as Wentworth State Park on the shore of scenic Wentworth Lake and the Cotton Valley Rail Trail, a 12-mile hard-packed trail for walking, cycling, wildlife viewing, and exploring railway motor cars.


The Newmarket Mills building in Newmarket, New Hampshire.
The Newmarket Mills building along Lamprey River in Newmarket, New Hampshire.

Fifteen miles from Portsmouth is the historic mill town of Newmarket. Incorporated in 1727, industries like textiles and shoe manufacturing flourished in the city thanks to its location along the Lamprey River. Today, visitors to Newmarket can walk or cycle along the picturesque riverside. Downtown Newmarket is full of unique shops and cafés like the Big Bean, who serve an endless coffee mug in the morning and an espresso mudslide in the evening, or Crackskull’s Coffee & Books, where they offer store credits for best-loved and slightly-used books.

For cultural travelers, the Stone Church, built initially as a meeting house in 1832, has a storied past. It was the first Catholic Church in Newmarket, a roller skating rink, and a playhouse, and then became The Newmarket Heel Factory during the town’s shoe-making heyday. The Stone Church became a music club in 1970 and is now a musical mecca in this small town, having hosted more than 15,000 shows and attracting musicians like Bonnie Raitt, Ritchie Havens, Suzanne Vega, Phish, and Carlos Santana.


Brick building along Main Street in Plymouth, New Hampshire.
Historic brick along Main Street in Plymouth, New Hampshire. Editorial credit: Wangkun Jia /

Plymouth is a small college town in the stunningly beautiful and rugged White Mountains. The highest point in the area, Plymouth Mountain, rises between Newfound Lake, the Tenney Mountain wind farm and ski area, and downtown Plymouth. It may well be the town’s best-kept secret as the few trails accessing it are mostly locally known. One of the most popular hikes is the Plymouth Mountain Sutherland Trail, a 4-mile out-and-back, moderately strenuous hike with an elevation gain of 1400 feet. Another outdoor activity in Plymouth is the nearby Polar Caves Park. The caves were formed during the Ice Age and named after the "polar" breath that emanates from the caves, even on the hottest summer day.

The town is also home to Plymouth State University, which hosts events such as concerts, theater performances, and art exhibitions open to the public. History enthusiasts can visit the Plymouth Historical Museum and stroll down its 19th-century Victorian Main Street, displaying numerous historical artifacts and large-scale scenes depicting a vibrant community. While in town, don’t miss the Flying Monkey Movie House & Performance Center in downtown Plymouth, which was originally a vaudeville and silent film theater. Today, the theater hosts folk, blues, and rock music, art exhibits, and community theater, yet it still pays tribute to its silent film past with its 2024 Silent Film Series, “L’ARGENT.”


Coast of Lake Winnipesaukee in Gilford, New Hampshire.
Scenic foliage along the coast of Lake Winnipesaukee in Gilford, New Hampshire.

Gilford offers a blend of natural beauty and historical charm. Visitors can explore the scenic shores of Lake Winnipesaukee, New Hampshire's largest lake at 71 square miles. “Lake Winni,” as the locals know, is a perfect location to enjoy the great outdoors. Visitors can set sail on a small sailboat or rent an inflatable pedal kayak from Fay’s Boat Yard. Moreover, there are many public beaches around the lake for swimming, including the 600-foot Ellacoya State Beach in Gilford.

On a clear day, above Lake Winnipesaukee, visitors can spot the White Mountains from the Gunstock Mountain Resort, a premier winter and summer destination in Gilford. The resort features miles of dog-friendly hiking trails, a stocked pond for fishing, mountain biking trails, and adrenaline-pumping activities at Gunstock’s Adventure Park. Some of the most popular activities are ziplining, traversing a 90-obstacle aerial treetop adventure, taking a mountain coaster ride, or a scenic chairlift ride to the summit.

Finally, Gilford is home to the BankNH Pavilion—an outdoor amphitheater that hosts a variety of concerts and events throughout the year. During the summer of 2024, visitors can catch Hootie & the Blowfish, New Kids on the Block, or Willie Nelson & Family as part of the Outlaw Musical Festival.


The River Walk Covered Bridge in Littleton, New Hampshire.
The River Walk Covered Bridge along the Ammonoosuc River in Littleton, New Hampshire.

Along the Ammonoosuc River, Littleton is a cute, cozy, and charming town with a main street worth exploring. Bursting with New England charm, there are so many funky and eclectic shops, like Chutters, a candy shop that holds the world record for the longest candy counter at 112 feet, and the Coffee Pot, which serves breakfast and lunch all day and still has time to bake fresh bread daily. Meanwhile, those looking to take back some souvenirs can stop to shop at the Bella Funk Boutique and Little Village Toy & Book Shop.

The Littleton Opera House has been a cultural landmark in the community since its construction in 1895. The opera house features stunning Victorian-era architecture, with a grand auditorium adorned with ornate detailing. Today, it continues to serve as a hub for arts and culture in the region. In the summer of 2024, it will host Studio Two, a Beatles tribute band voted “The Best Beatles Tribute Band in New England” by The Boston Globe.


Bridge in Peterborough, New Hampshire.
Riverside view of a bridge in Peterborough, New Hampshire.

As one of New Hampshire’s oldest towns, Peterborough (founded in 1737) is a cute town surrounded by luscious forests and stunning scenery. It is perhaps most well-known as the location of MacDowell, which, until 2020, was known as “The MacDowell Colony.” Founded in 1907 by renowned composer Edward MacDowell, MacDowell is an artists’ retreat providing residencies for hundreds of artists annually. Its alum list includes composer Leonard Bernstein, playwright Thornton Wilder, and writer Jonathan Franzen. An art town through and through, Peterborough is also home to the Mariposa Museum & World Culture Center and numerous local downtown art galleries.

Established in 1891, Miller State Park in Peterborough is the oldest state park in New Hampshire. It spans over 500 acres and offers scenic views of the surrounding countryside and Mount Monadnock. The park is known for its extensive network of hiking trails, including the Wapack Trail, a 21-mile footpath. Standing at an elevation of 3,165 feet, Mount Monadnock offers panoramic views of the surrounding landscape, including the Wapack Range, the Monadnock Region, and the distant Boston skyline on clear days. After Mount Fuji in Japan, Mount Monadnock is the second most summited mountain in the world.


The six cute small towns of Wolfeboro, Newmarket, Plymouth, Gilford, Littleton, and Peterborough in New Hampshire offer a delightful mix of history, natural beauty, and charming attractions. From the oldest summer resort in America to the longest candy counter in the world to the second most summited mountain in the world, New Hampshire has a lot to offer visitors in 2024. Moreover, visitors can take in the views without the hustle and bustle of urban centers.

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