Experience the Magic of Fall with Fairs, Festivals and Family Fun in the Valley

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It’s no secret that the Valley is home to some of the best leaf peeping in the country. But when you plan your trip to see the foliage, be sure to check out some of the events that bring the region’s small-town charm to life. Here’s your guide to some of the most anticipated events of the season that showcase the spirit of this region. 

Pull out the calendar and start planning your fall getaway around these exciting fall festivals, fairs, and fundraisers! Have a ball this fall with foliage and family fun!

Settlers Green

Busker Festival  — Shoppers will discover music around every corner with more than a dozen street musicians filling the autumn air with the sounds of bluegrass, jazz and rock. Held each October, this annual event transforms the area into a lively open-air stage.

Bring A Friend — Settlers Green’s signature shopping celebration is one of New England’s most anticipated shopping events. Each November, the 10-day extravaganza features daily events, entertainment, extended store hours, giveaways and more. 

Fryeburg Fair 

Located in Fryeburg, Maine, this is a hybrid of a food festival, livestock show, 4-H competition, and carnival, complete with rides and games. Spanning 185 acres, it draws more than 220,000 visitors each year and kicks off in late September. 

There are countless reasons to visit the Fryeburg Fair, but the food is what keeps many coming back year after year. Vendors serve up favorites like pizza, fried dough, loaded baked potatoes, apple crisp, glazed donuts, turkey legs and more.

Visitors can also enjoy special events, such as the Skillet and Anvil Throw, Firemen's Muster, or Sheepdog Trials, along with daily live entertainment featuring an impressive lineup of musicians.

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Sandwich Fair 

In mid-October, this traditional agricultural fair features thrilling rides, entertainment, live music, agricultural exhibits, crafts, parades and delicious food. Events over the three days will include Children’s Day, Family Day, and Monday is Senior Citizen/4H/Military Day, with free admission for active or retired military.

‍Now in its 115th year, The Sandwich Fair is one of New Hampshire’s longest-running agricultural fairs. Plenty of free and paid parking around the historic small town makes the Sandwich Fair an easily accessible, fall foliage adventure to plan for.

Return of the Pumpkin People 

Each year, a highlight of the foliage season is The Return of the Pumpkin People. Businesses throughout Mt. Washington Valley create displays of pumpkin people; the only requirement being that the heads are made of pumpkins. Take a self-guided tour of the pumpkin people and vote on your favorites. Maps are available at participating properties and online at JacksonNH.com.

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Fall Fests and Fairs

Ledge Brewing Company — Their annual Ledgetoberfest includes live music, a keg rolling contest, an Oktoberfest Beer Mile, a stein holding contest and a Best Dressed Award. 

Attitash Mountain Oktoberfest – Get ready for a fun-filled day of live music, local eats, a Biergarten, and fan-favorite competitions like stein hoisting and a keg toss. There are also activities for the kids, including crafts, games, face painting and more.

Tuckerman Brewing — Their annual Fall Fest will feature live music and food trucks as well as contests like axe throwing, a stein hoist and a keg toss with prizes for the winners. 

Cranmore Mountain Resort — Their annual Hay Day Fall Fest on the Fairbank Lodge Patio and lawn is a family-friendly celebration of all things fall. Enjoy activities like caricature artists, axe throwing, candy apple decorating and a beer garden.  There will also be a variety of contests throughout the day, such as Donut on a String, Whipped Cream Pie Eating, a scavenger hunt and much more.

Purity Springs Resort Oktoberfest — Set against the picturesque backdrop of Purity Island, this event takes place in late September. Grab a party partner and enjoy an array of traditional German fare, beer, stein hoisting and music.

Kula Yoga Fest — This three-day event held over the Autumn Equinox features inspiring yoga classes, holistic well-being workshops, nature immersion and community connection. Reserve your spot online as they are limited. 

Mt. Washington Valley Fall Craft Fair — In early October, over 100 local artisans display a wide array of media, including handcrafted jewelry, candles, woodworking creations, photography, soaps, metal art, books, pottery and much more. Located in Schouler Park, admission is free and leashed pets are welcome. Also, enjoy live music and local eats throughout the weekend.

Leaf Peeper’s Craft Fair — Taking place at the peak of foliage season, this two-day craft fair is located in Schouler Park, where over 120 local artisans bring the fall season to life through their creations. Enjoy free admission, live music and food. Leashed pets are welcome.

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For more info on what’s happening around the Valley, visit our Events Calendar.

To learn more about New Hampshire vacations, go to www.VisitNH.gov.