4 Quintessential small towns to experience summer adventure in New Hampshire

Hike to great heights or visit unique local markets in one of these inviting northeastern locations.

Photograph by Jody MacDonald
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Alyson’s Orchard features over 50 varieties of apples, along with berries, peaches, grapes, pears and plums.

Photograph by Jody MacDonald

4 Quintessential small towns to experience summer adventure in New Hampshire

Hike to great heights or visit unique local markets in one of these inviting northeastern locations.

With the blooms of the season adding color to every mile and the friendly smiles of locals welcoming visitors every which way, it’s easy to feel at home in the Granite state. But it isn’t just nature that makes New England a must-see destination — it’s the tiny cities woven throughout the rolling green hills. All New Hampshire roads can bring you to another new small town. From Jaffrey to Walpole, consider this your guide to some of the most quintessential small towns in New Hampshire.


Located in the Monadnock Region of New Hampshire, Keene is home to Keene State College. Lined with brick buildings and trees, this town is growing alongside the next generation, with a plethora of shops and restaurants catering to a younger crowd. The Hannah Grimes Marketplace features artisan goods, crafts, beer and wine from locals, while the female-owned shop Prime Roast Coffee Company fires up beans from all over the world right in the city limits. This summer, they’re inviting artists to create murals throughout the town at the Keene Walldog festival, adding a modern, dynamic vibe to the streets.

Nearby, don’t miss a visit to the many swimming holes, including Surry Lake, Spofford Lake, and Otter Brook Lake Park. Mt. Monadnock, one of the most climbed mountains in the country, is also easily accessible and offers camping, hiking trails for those more experienced, picnicking, and a myriad of protected highlands to fawn over.


Blink and you might miss Walpole, east of the scenic New Hampshire Route 12. When you think of small-town living — that’s what you’ll find in this (super!) small town. Many years ago, the town decided to move its main street, which then created a grand entrance for drivers passing through: gorgeous brick houses with sprawling views of the countryside and mountains as the backdrop. It’s a short, 10-minute drive from Alyson’s Orchard — a year-round destination for families and travelers with a captivating backstory.

The owner, Susan Jasse, has a degree in chemistry and microbiology — and she used it to work at Harvard Medical School and Tufts University. But even with her impressive pedigree, she admits she never really liked it. What she loved was food, which ultimately led her to work at Le Bocage in Boston, and then in the countryside after she met her husband, Bob, who owned the land and opened Alyson’s Orchard. This spot, with its homey vibes, has become a sought-after wedding venue and family retreat. In the summer, the orchard comes alive with blueberries, sour cherries, raspberries and peaches, and their market sells pies and sweet treats from the land.

Half an hour away is Madame Sherri’s Castle Ruins, where you will stand in awe of an ancient stone staircase leftover from almost a century ago. Named after Madame Antoinette Sherri, a costume designer in the 1920s, this 488-acre area is dotted with hiking trails. One of the most famous is Ann Stokes loop, a 2-mile trek around the forest with views of Indian Pond and Chesterfield. One more thing: before you head off to your next stop in New Hampshire from Walpole, grab a coffee, pastry and chocolate mousse from the legendary L.A. Burdick Chocolate.

Closeby is Chesterfield Gorge, a 13-acre state park along Route 9, offering trails, waterfall views, and picnic areas. There are numerous hikes throughout this gorgeous, mostly-shaded area, thanks to a collection of hemlock trees and natural brooks. Most visitors make the journey to see Wilde Brooke, which has waters rushing from the rocky gorge that pool into a pond, eventually leading to the Connecticut River. During the summer months, you’ll find plenty of fellow hikers exploring the path — which can take you over and under tree stumps, through bushes and more.


Even though it is only 38 square miles, Peterborough's charming downtown offers easy-access to many trails and mountains nearby. While you’re driving through the streets, look out for their historical landmark — the Peterborough Library, which was the very tax-supported book house in the United States. Wet your whistle or carb-load before a big adventure at the Peterborough Diner, infamous for its iconic lunch-car shape and style from the 1950s.

If you have an interest in antiquing, Twin Elm Farm may be your decor-haven. This converted farmhouse from the 1800's is now filled with vintage furniture, home accessories, and unique treasures.


If you’re looking for a romantic getaway, or prefer to stay at a B&B, Jaffrey may be ideal for your getaway to New Hampshire. Its central location connects to many quaint inns surrounded by nature, including Monadnock Inn and Woodbound Inn. For local eats, consider Sunflowers or Lab ‘N Lager, and for a classic, charming New England supper, book a reservation at Kimball Farms.

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Cathedral of the Pines, an open-air chapel, is open to the public and sits on 236 acres.

Eight minutes from Jaffrey and just outside Annett State Forest, the history of Cathedral of the Pines is fascinating and immense. Seventy-five years ago, a family purchased the property, hoping their four children would build homes on the land. As they navigated the grounds, they found a stone in the shape of a Bible and had the idea of an open-air chapel where others could come to worship. It is an official national memorial for fallen soldiers and a multi-faith cemetery that has attracted notable visitors like Barack Obama and Harry Truman. But if you ask the executive director, Patricia Vargas, this sacred space offers something for everyone.

Nearby, two hiking trails — one three miles, another five — offers views of Monadnock Region, and a picnic area makes a great spot for families. The uninterrupted blue skies and the open invitation to all religions make it a place to explore — and catch your breath.

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