Southern New Hampshire Hiking Guide (From Easy to Challenging!)

Enjoy the natural beauty of the outdoors and explore the best of local hiking in and around Chesterfield with this innkeeper-curated guide to nearby trails. Judy has put together a list of her personal favorites for every type of adventurer and skill level. Make lasting memories with a stay at Chesterfield Inn in New Hampshire and see everything the area has to offer!

Man hiking in New Hampshire

West River Trail

  • 15 Minutes Away
  • Difficulty: Beginner 
  • Dog-Friendly

A beautiful and scenic hike in Brattleboro that follows the West River, the aptly named West River Trail is a perfect hike for beginners or those looking for a casual sightseeing trip. Nestled amongst trees and wildflowers, the trail follows a former railroad track and winds its way through over 18 miles of Vermont countryside. Restoration efforts have been ongoing since 2011 for the lower sections of the trail and more sections continue to be worked on every year for even more places to hike, bike and sightsee.

a family hiking a trail going up a mountain

Mount Wantastiquet

  • 15 Minutes Away
  • Difficulty: Beginner-Intermediate

Experience unforgettable views from the top of Mount Wantastiquet on this unique trail in Hinsdale. Located in a gorgeous state forest, it starts off with an easier part of the trail that makes its way past a waterfall! Afterward, follow a series of switchbacks up to the summit and catch a glimpse of the Connecticut River and Battleboro below. This trail moderately increases in difficulty once the ascent begins but it is still very doable by hikers of most skill levels. Highly recommended for its stunning views of the surrounding area.

the famous staircase in the ruins of the Madame Sherri house

Madame Sherri Forrest

  • 10 Minutes Away
  • Difficulty: Intermediate
  • Dog-Friendly

Home to the famous Madame Sherri’s “castle,” the ruins of the once-great house can be found in the forest named after its namesake. Take the nearby trail and explore the picturesque woods surrounding the property. Once you’ve had time to explore the ruins, continue on and make the climb up to Indian pond to end your adventure with a splash! A unique trail that showcases an interesting element of local history here in Chesterfield, all while providing a beautiful backdrop for a morning or afternoon hike.

a group of people hiking in a forest

Pisgah State Park

  • 10 Minutes Away
  • Difficulty: Beginner-Intermediate
  • Dog-Friendly

Easily worth the drive to get there, the natural ambiance of the state park is a sight to behold. 21 square miles of wilderness hold many trails and paths to take, but we personally recommend the Fullam Pond Trail. Park at the Horseshoe Road entrance and take the Fullam Pond Trail to the Lily Pond Trail and back for a vigorous hike through the dense forests of the area. Some experience in hiking is required as much of the land within the park is considered rough terrain, so don’t forget those hiking boots!

view from the summit of mount monadnock

Mount Monadnock

  • 45 Minutes Away
  • Difficulty: Intermediate

An all-day affair in Jaffrey, this hiking adventure is not for the faint of heart or inexperienced! Tackle the intense but rewarding climb to the summit of Mount Monadnock and be rewarded with absolutely stunning views of the area; you can even see Boston on especially clear days. Reservations are now required for this excursion so remember to claim your spot and prepare for a 3 – 4 hour roundtrip hike on difficult uphill terrain. Afterward, you can sit back and make up for all those burnt calories with a delicious dinner at the Chesterfield, after making it to the summit you’ve certainly earned it!

fireplace and sitting area in Chesterfield, NH guest room

Rest your weary bones in one of our comfortable and spacious rooms after a full day exploring the great outdoors! Warm-up by the fireplace with a glass of wine and enjoy elegant accommodations with a cozy New England design aesthetic. In addition, we have pet-friendly rooms available so you can stay with your furry friend! Many of our nearby trails allow dogs so you can embark on adventures with your faithful companion right alongside. Start your next day of hiking with a fresh breakfast made from fresh ingredients sourced from nearby farms and get ready to take on another day of fun in the Chesterfield sun! We hope this guide has helped you find the right hike and look forward to seeing you at the Inn.

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