Littleton, New Hampshire. Editorial credit: Eli Wilson / Shutterstock.com

7 Most Unconventional Towns In New Hampshire

New Hampshire is known as the perfect weekend getaway because it borders many accessible cities, such as Boston, Massachusetts, and Vermont. If you are looking for an off-beat trip, New Hampshire offers many unseen jewels to discover. From unorthodox activities such as exploring old Victorian-style mansions to visiting the longest candy counter in the world, New Hampshire will take you on an adventure no other place can offer. If you would like a low-key hideaway, New Hampshire has many highly regarded literary towns visited by famous writers such as Thoreau and statues erected in their memory, such as Eleanor H. Porter—and libraries full of uncommon books. These top seven towns tick many boxes of New Hampshire's most unconventional towns.

Keene

Keene, New Hampshire
Carved pumpkins on display at a festival in Keene, New Hampshire. Editorial credit: James Kirkikis / Shutterstock.com.

Keene is one of the most unusual towns in New Hampshire. It is known for its progressive culture and creative festivals—The Toadstool Bookshop is an independent bookstore that regularly hosts literary events for the town while doubling as a cafe space with a rather sizeable eclectic book section. The Keene Pumpkin Festival is a yearly seasonal event showcasing thousands of lit pumpkins, some of which have made it to the Guinness World Records. It is visited by many. Cheshire Railroad Station and the Horatio Colony House Museum are dedicated businesses to Keene town's history of railways and artifacts from one of the local families in the 19th-century preserved home.

Sugar Hill

St. Matthew’s Chapel in Sugar Hill, New Hampshire.
St. Matthew’s Chapel in Sugar Hill, New Hampshire.

Sugar Hill was named for the backdrop of the town's centuries-old maple tree groves, which has given it the title of one of the most historic communities in New Hampshire. After winter has turned, it’s maple syrup season in Sugar Hill—Pollys Pancake Parlor has operated since 1938 and serves local maple syrup with every meal. Not only is the syrup of the old world in Keene, but Harmans Cheese and Country Store is also famous for its world-class aged cheddar, which is named the world’s best by its loyal customers. The Sugar Hill Historical Museum and the Historic White Mountain Resorts display artifacts and present remnants of the golden era of mountain hotels in the area—some of which predate the 1800s.

Dublin

The church and rotary in the center of Dublin, New Hampshire
The church and rotary in the center of Dublin, New Hampshire. Image credit: Magicpiano via Wikimedia Commons.

Dublin is a quaint town in the foothills of Mount Monadnock known for its intellectual pursuits. Woodland trails and lakes surround the area, which has been a pre-loved hiking spot by famous transcendentalist writers such as Thoreau and Emerson. Yankee Publishing Headquarters resides in Dublin, home of the Old Farmer’s Almanac. The headquarters offers tours and insights into the business’ iconic publications past. The Dublin Day School is a progressive dual boarding and day school, sitting on 500 acres of hilltop offering panoramic views of the whole town. The Dublin Lake Club is a private club and icon of the town's social history—providing status and reputation.

Exeter

Aerial view of the historic town center of Exeter, New Hampshire.
Aerial view of the historic town center of Exeter, New Hampshire.

Picture a photo-worthy small downtown scene where trees perfectly line the streets, the buildings an array of color and age, and a river winding through the town, and you will have Exeter. The Phillips Exeter Academy Bookstore harnesses the authentic New Hampshire unconventional vibe through its book collection of rare and contemporary finds. Exeter has a rich history dating back to 1638, is the Revolutionary War capital, and is one of the most historic communities in New Hampshire. The town has several figureheads in ode to this deep-rooted history, such as The American Independence Museum, Exeter’s Revolutionary War Grades, and The Gilman Harrison House—each showcasing original war documents, artifacts, and insight into colonial life and trade.

Littleton

the Ammnosuoc River in Littleton New Hampshire
The Ammnosuoc River in Littleton, New Hampshire.

Littleton is a small town in the heart of the White Mountains that boasts literary and confectionary delights. It is home to Chutters, a candy store with the world's most extended candy counter and every candy, chocolate, caramel, and fudge you could think of. There is something for everyone. The Riverrock Covered Bridge overlooks the Ammonoosuc River and the town, offering a perfect picture moment for your trip highlights. The Pollyanna Statue greets many of the town's residents and travelers and celebrates Eleanor H. Porter, a famous author from Littleton who wrote the children's classic book Pollyanna in 1913. Historic displays and artifacts of Littleton's industrial and cultural history can be found at the Historical Society Museum, which initially started as a public library but is now the caretaker of Littleton's past and present.

Harrisville

Harrisville, New Hampshire
A 19th-century textile mill in Harrisville, New Hampshire.

In the heart of the Monadnock region is Harrisville, one of New Hampshire's historic communities, a town seemingly frozen in time. The town is centered around a landmark industrial mill complex, one of which is Harrisville Designs. An old mill turned into a weaving studio, Harrisville Designs sells high-quality yarn and looms and has yearly workshops and curriculums. Harrisville Historic District is a national landmark that devotes itself to the textile mill heritage of Harrisville and aims to revitalize, maintain, and preserve the town's historic sights. Old Brick Church is a Greek revival-style building dating back to 1844 and is essential to the town's heritage. Stretching over 138 acres, Harrisville Pond provides outdoor activities such as kayaking and fishing and is an ideal spot for photography.

Portsmouth

Portsmouth, New Hampshire.
Aerial view of Portsmouth, New Hampshire.

Portsmouth is known as one of New Hampshire’s most unusual towns. It is the oldest settlement in New Hampshire, dating back to the 17th century—yet it also has lots of modern charm. A coastal gem, Portsmouth is rich in maritime history and has a buzzing arts scene downtown. The Music Hall is a Victorian-era theatre and is dubbed one of the most vibrant destinations in New Hampshire, hosting concerts, plays, and literary talks. Portsmouth has history bursting at its seams. Visit the Strawbery Banke Museum to view the living history of Indigenous peoples, which has artifacts dating back over 10,000 years, or Albacore Park, a national historic landmark of a navy submarine that offers visitor tours for greater insight. The Portsmouth Harbour Lighthouse is one of the town's landmark beacons that offers guided tours and fantastic photo opportunities.

March To Your Own Drum In New Hampshire

Whether you want a historic-based, eccentric, or unconventional trip, each of these seven towns offers many options. From learning about the centuries-old history on the grounds of Portsmouth, entering sugar maple land at peak season and finessing maple syrup of your own in Sugar Hill, or viewing the outdoor glory of Littleton overlooking the mountains while eating 50 kinds of candy, New Hampshire beats to its own drum and welcomes those who do, too.

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