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Monadnock Region

Your fall road trip itinerary for the Monadnock region.
Scenic roads with mountain views, quiet orchards with apples for miles, foliage-drenched landscapes… it must be fall in the Monadnock Region. Hop in the car and explore this peaceful region of the state, where wholesome adventures and classic fall memories are just around the corner.

Check out New Hampshire’s estimated peak foliage dates to time your trip just right, or stay updated on conditions via weekly foliage reports.

  1. Milford Pumpkin Festival (Milford) Each year, the town of Milford is illuminated by the glow of hundreds of jack-o-lanterns during the annual Pumpkin Festival, set for October 6-8, 2023. In a massive celebration of the season, attendees can sample local beer and wine, witness a pumpkin catapult, watch a rubber duck race, make a scarecrow, explore a haunted trail, and so much more!

  2. Washburn’s Windy Hill Orchard (66 Mason Road, Greenville) Washburn’s Windy Hill Orchard is the perfect place to make fall memories. Here, you can get lost in a corn maze, pick your own apples straight from the orchard, treat yourself to fan-favorite seasonal soft serve or indulge in some of the best apple cider donuts around!

  3. Monadnock State Park (169 Poole Road, Jaffrey) Mount Monadnock is the heart of New Hampshire’s southwestern region, and its beauty has inspired the famous works of Robert Frost, Thornton Wilder, and Henry David Thoreau. In autumn when the mountain is ablaze in fall colors, it’s truly a sight to behold.

  4. Monadnock Region Covered Bridge Tour (181 Sawyers Crossing Road, Swanzey) The Monadnock Region hosts a collection of seven of the state’s historic covered bridges, with four of them in the town of Swanzey alone! Follow along this charmingly scenic route that will tour you through foliage-framed roadways and the romantic covered bridges that are a hallmark of the Granite State.

  5. Branch and Blade Brewing Company (17 Bracado Street, Keene) Since 2018, founders Trevor and Jesse have been crafting up unique brews with seasonal flavors and high-quality ingredients. Stop in and try a brew for yourself after a day of fall exploring!

  6. Flying Pig Antiques (867 Rt. 12, Westmoreland Industrial Park, Westmoreland) Browse through the region’s history as you sort through the shelves of treasures at Flying Pig Antiques. Is there any better way to spend a chilly autumn afternoon than hunting for vintage antiques in one of the oldest parts of the country?

  7. Franklin Pierce Homestead Historic Site (302 2nd NH Turnpike, Hillsborough) Step back in time to a replica of affluent living in the nineteenth century as you explore the former home of the 14th president of the United States, Franklin Pierce. Tours of the historic homestead are offered on weekends throughout the fall season.


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