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Fall Fairs and Fests in Mt. Washington Valley


Applauded by media with accolades like “most spectacular places for fall foliage” by Buzzfeed and “Best fall destination” by TripAdvisor and USA Today/10 Best, Mt Washington Valley and the White Mountains are a popular fall vacation choice.

It’s no wonder why. Mother Nature simply never disappoints with her harvest hues painting a patina across the mountains. There are so many ways to peep a leaf in Mt Washington Valley, and that’s reason enough to come.  

Add in special fall festivals, family fun, foliage and fairs throughout the Valley and it’s no wonder this is such a popular vacation destination. We always advise visitors to ‘book now or forever hold your peep”.  With more than 150 lodging properties in the Valley, there’s always room for fall visitors, but it gets harder and harder to find availability the closer you get to peak foliage (usually coincides with Columbus Day but varies by weather each year).

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!

Fall Fest at Settlers Green: Experience the best of fall in the White Mountains with family-friendly fun at Settlers Green's annual Fall Festival on September 25th. Featuring a Candy Pumpkin Guessing Contest, complimentary apples on the green, a kids hay maze and pumpkin painting as well as fall displays.

Live Music featuring String Equinox will be ongoing from 11am to 1pm "on the green" in the Courtyard. Live Music featuring String Equinox will be ongoing from 11am to 1pm The oh-so-talented Shana Aisenberg and Beverly Woods duo String Equinox is back this year! Beverly specializes in playing the hammered dulcimer and Shana specializes in the violin. Seating will be provided to sit in and enjoy.

Settlers Green is also hosting the Busker Festival on October 9th and 10th, as well as the Boo Bash on October 29th!

It's also important to save the date for Settlers Green's famed annual shopping event, Bring a Friend. The perfect girls getaway, enjoy shopping deals, great dining experiences, giveaways and entertainment. Shop the best names in fashion with added festivities to make it an experience you'll turn into tradition.

Settlers Green is hosting a myriad of fall events, including its well known Bring A Friend shopping event happening in November.

Our 21st Annual Bring A Friend event will take place over 10 days, November 5-14, 2021, with the bulk of activities taking place November 11-14, 2021, and Saturday, November 13 being the primary day for festivities.

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. It sits on 185 acres of land, is spread across 100 buildings, and attracts over 220,000 people annually.

While there are many reasons to visit the Fryeburg Fair, many come for its food scene. People wait all year for the vendors who are famous for their pizza, fried dough, loaded baked potatoes, apple crisp, glazed donuts, turkey legs, and more. Many visitors make special relationships with individual vendors, and return year after year to see the same bakers and chefs for their signature fair food.

Enjoy taking in special events such as the Skillet and Anvil Throw, Firemen's Muster, or Sheepdog Trials, as well as daily live entertainment with an impressive lineup of musicians.

The Sandwich Fair is one way to experience the quintessential New England life this fall in Mt. Washington Valley!

Sandwich Fair: Happening October 9th through October 11th, this traditional agricultural fair features thrilling rides and midway concessions, music and entertainment, agricultural exhibits, crafts, parades, and delicious food. Events over the three days will include parades, Children’s Day on Saturday, and Family Day on Sunday. Monday is Senior Citizen/4H Day, with free admission for active or retired military.

A new cornhole tournament is being planned for Friday night, Oct. 8th, always a favorite competition for New Englanders! Two longtime favorites, the Granite State Disc Dogs, and miniature horses, will also be returning to the 2021 fair.

Another exciting fair highlight is the Sunday afternoon parade. This year’s parade is dedicated to the Alfred J. Quimby Fund, which has generously funded and supported the town of Sandwich and its residents since 1918.

Now in its 110th year, The Sandwich Fair is one of New Hampshire’s longest running agricultural fairs. It draws thousands of visitors from around New England for the Columbus Day weekend event. Plenty of free and paid parking around the historic small-town makes the Sandwich Fair an easily accessible, fall-foliage adventure to plan for.

Make your way from village to village as you take in the creative masterpieces of each business' Pumpkin People entry!

Return of the Pumpkin People: Each year, a highlight of foliage season is "The Return of the Pumpkin People" now in its 32nd year. Businesses throughout Mt. Washington Valley create whimsical 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 favorite from Oct 1-31, 2015. At least a dozen of the pumpkin people will be located at Settlers Green. Maps available at participating properties and online at

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