MONADNOCK REGION, N.H. (MyKeeneNow) Crisp mornings, blazing foliage, and the smell of cider doughnuts in the air — fall in New England means festival season. The Monadnock Region and neighboring southern Vermont come alive with music, food, art, and plenty of pumpkins. Here’s your guide to some of the biggest and most beloved events this season.

Harvest Celebration at Alyson’s Orchard — Walpole, NH

Sunday, Sept. 21, 9 a.m.–4 p.m.
Alyson’s Orchard, 57 Alyson’s Lane, Walpole
Free admission

Alyson’s Orchard kicks off the season with its annual Harvest Celebration, a day of family fun surrounded by rolling orchards and mountain views. Visitors can enjoy pumpkin carving, apple chuckin’, kids’ games, food vendors, and more. The farm store will be stocked with apples, cider, and fresh baked treats.

Winchester New Hampshire Pickle Festival — Winchester, NH

Saturday, Sept. 27, 10 a.m.–4 p.m.
Main Street, Winchester
Free admission

The 27th annual Pickle Festival is back, and it’s brinier than ever. Main Street fills with vendors, music, food stalls, and of course, pickles of every variety. A pickle parade, pickle-eating contest, and family-friendly activities make this one of the quirkiest — and most popular — fall events in the Monadnock Region.

Keene International Festival — Keene, NH

Saturday, Sept. 27, 11 a.m.–3 p.m.
Keene Parks and Recreation Center, 312 Washington St.
Free admission; donations welcome

This community festival celebrates the cultural diversity of the region. Sample international foods, shop handmade crafts, and enjoy music and dance performances representing traditions from around the world. Interactive booths and activities ensure fun for the whole family.

Oktoberfest at Walpole Grocery — Walpole, NH

Saturday, Sept. 27, noon–9 p.m.
Walpole Grocery, 47 Main St.
Free to attend; food and drinks available for purchase

Raise a stein at Walpole Grocery’s lively Oktoberfest. The daylong event features German-inspired fare, local beers, and festive music. It’s a great place to soak up the autumn atmosphere with friends and neighbors.

Chester Festival on the Green — Chester, VT

Saturday–Sunday, Sept. 20–21, 9 a.m. to 5 p.m.
Downtown Chester
Free admission

This classic Vermont village festival takes over the town green with artisan vendors, food stands, historic home tours, and live performances. The setting — Chester’s picture-perfect green — provides a quintessential backdrop for a weekend of browsing crafts, listening to music, and sampling regional specialties.

Deerfield Fair — Deerfield, NH

Thursday–Sunday, Sept. 25–28, 8 a.m. to 10 p.m. (25-27) and 8 a.m. to 7 p.m. (28)
Deerfield Fairgrounds, 34 Stage Road
Adults $12; seniors $9 (Thu–Fri); ages 12 and under free

In its 148th year, the Deerfield Fair remains one of New England’s largest agricultural fairs. Expect livestock barns, 4-H competitions, craft displays, carnival rides, fair food galore, and live entertainment on multiple stages. It’s a true celebration of rural heritage with something for everyone.

Fall Festival & Chili Cook-Off — Claremont, NH

Saturday, Oct. 4, 10 a.m.–3 p.m.
Visitor Center Green, Claremont
Free admission; chili sampling fees apply

Claremont’s Fall Festival combines live music, food trucks, vendor booths, and family activities with the irresistible aroma of simmering chili. Sample entries in the chili cook-off and cast your vote for the best. The event also includes races and games for kids, making it a favorite community gathering.

Oktoberfest at East Hill Farm — Troy, NH

Sunday, Oct. 5, beginning at 5 p.m.
Inn at East Hill Farm, 460 Monadnock St.
Reservation required; BYOB

East Hill Farm hosts a cozy, traditional Oktoberfest with hors d’oeuvres at 5 p.m., dinner at 5:30 p.m., and live oompah music. Guests can enjoy hearty German fare in a relaxed farmhouse setting.

Monadnock Art Open Studio Tour — Monadnock Region, NH

Saturday–Monday, Oct. 11–13, 10 a.m.–5 p.m.
Studios across Dublin, Hancock, Harrisville, Jaffrey, Marlborough, Peterborough, and Sharon
Free admission

The region’s oldest and largest art tour invites visitors to explore more than 60 artists’ studios. Pottery, painting, woodwork, and glass are just some of the media represented. The tour doubles as a scenic drive through colorful backroads and historic villages, with many works available for purchase.

Fall Foliage Art Studio Tour — Monadnock Region, NH

Saturday–Monday, Oct. 11–13
Self-guided tour
Free admission

Another self-guided art tour brings visitors to local studios across the Monadnock Region. Artists open their doors to share their creative process and offer works for sale, making this both an art experience and a chance to enjoy peak foliage season.

Heirloom Apple Day at Scott Farm — Dummerston, VT

Sunday, Oct. 12, 10 a.m.–5 p.m.
Scott Farm Orchard, 707 Kipling Rd.
Free admission

Scott Farm’s annual celebration showcases more than 130 varieties of heirloom apples. Tastings, orchard tours, storytelling, food vendors, and children’s activities make this a delicious and educational fall outing.

Dummerston Apple Pie Festival — Dummerston, VT

Sunday, Oct. 12, 9:30 a.m. until sold out
Dummerston Congregational Church, 1535 Middle Rd.
Free admission; food for purchase

Now in its 55th year, this festival draws crowds for homemade pies, cider donuts, Grafton cheese, and ice cream. Whole pies and slices are sold until they run out, and the event happens rain or shine under a large tent.

Keene Pumpkin Festival — Keene, NH

Saturday, Oct. 18, 2 p.m. until dark
Downtown Keene
Free admission

Thousands of carved pumpkins light up Keene’s downtown streets in this beloved community tradition. The Pumpkin Festival also features food vendors, local performers, games, and family-friendly activities.

Peak into Peterborough — Peterborough, NH

Saturday, Oct. 18, 10 a.m. to 4 p.m.
Downtown Peterborough
Free admission

Peterborough celebrates the season with a lively fall festival downtown. Expect family activities, food, vendors, and a festive autumn atmosphere.