Now that autumn is beginning to show its true colors across the Cape’s stunning landscapes, and pumpkin spice is officially back on the menu, it’s time to slow down the hustle and give a proper welcome to the harvest season with family and friends. Here’s the local roundup of outdoor festivals and events that make it easy to plan a cornucopia of fall outings!   

Harwich Cranberry Arts & Music Festival
Saturday, September 18 and Sunday, September 19
Kick-off the season and support over 100 vendors selling unique, handmade items and crafts at this celebrated September artisan market and music festival. Enjoy this year’s live music lineup at the CranJam, and step onto the wooden dance floor under the tent when the spirit moves you—rain or shine! Bring a blanket or chair to stay awhile and make some new friends, get reacquainted with your favorite food truck menus, and don’t miss the Saturday fireworks at dark!  

Cape Cod Canal Day
Saturday, September 18
Any day that celebrates the beautiful Cape Cod Canal is a great day in our books. Buzzards Bay Park plays host to food trucks, live music in the gazebo, kids’ activities and a 5k road race. Sample craft beer and wine, peruse the work of local crafters and compete in a heated corn hole tournament.

Cape Cod Brew Fest
Saturday, September 25
Head to the Cape Cod Fairgrounds in Falmouth for the ninth annual beer festival celebrating American craft brewers from 50 + breweries, featuring over 200 distinct styles of beer. General admission tickets include unlimited samples, live music, access to food vendors & trucks, and a branded, custom pint glass to take home! Don’t forget to reserve a discounted Designated Driver ticket so you can safely enjoy and support the craft brew industry. On-site event swag and merch for sale make this a fall fest to remember!

Love Local Fest
Sunday, September 26
Shopping local has never been as fun as one of Love Live Local’s Love Local Fests. Held three times a year, the fall edition of this free fest will be held on the Hyannis waterfront at Aselton Park. Peruse the work of 75+ Cape Cod makers, artisans, artists and farmers, as local entertainers and a craft beverage garden set a lively vibe. Bring the kids because Cape Cod Maritime Museum will be hosting maritime-themed family activities on their back patio!

Mashpee Oktoberfest
Saturday, October 2
Brush up on your Oktoberfest lingo at home, then come out to the Mashpee Commons Village Green to celebrate fall with a day of merry-making and fun activities the whole family will enjoy. Delight your kids with the art of face painting and carnival games, watch them leap on the moon bounce, peruse over 50 craft booths, savor delicious food, and raise another glass to autumn at the authentic German Bier Garten featuring live music…and a stein race? Worth investigating!

Vinegrass Music Festival
Sunday, October 3
Gather around the vines with friends surrounded by the natural beauty of Truro Vineyards for a memorable day spent listening to American Roots Music. The 7th annual Vinegrass Festival lives on, bringing the roots genre of music and authentic sounds of Americana, bluegrass, and folk right to your backyard! Support this nonprofit along with an all-star lineup while you sip the vineyard’s signature wines and spirits, order from the food truck, and bask—or perhaps even dance—in the golden autumn light of the Outer Cape
Pumpkin Day at Bourne Farm
Saturday, October 9
Plan a perfect fall day with your kids on the beautiful grounds of the historic Bourne Farm nature sanctuary in West Falmouth, where you can pick your own pumpkins, say hello to the animals at the petting zoo, or take an old-fashioned hayride—one of the best ways to admire the colorful landscape and changing leaves. Pony rides, autumn-inspired crafts, a bounce house, and the perfect backdrop for a fall photoshoot make it easy to have a ‘Yes Day’ focused on family fun without too much planning! Keep everyone fueled with lunch available for purchase and a classic bake sale table!

Yarmouth Seaside Festival
Saturday, October 9 and Sunday, October 10
Join your neighbors at this favorite local gala event of days gone by, founded in 1978 and jam-packed with fun and entertainment for all ages. Arts and crafts, rides and games, delicious food, and live music and shows take center stage at this year’s comeback event that includes two days of scheduled activities, The Yarmouth Seaside Festival 5K along the Bass River, and a fireworks display on Seagull Beach. Check out the online schedule for family favorites like the kid’s rotating Mad Science and Animal Adventures tent shows, old-fashioned field day races, and even a pie-eating contest!

Chatham's Pumpkin People in the Park
Oct 15-31
Take a seasonal stroll to admire the fascinating pumpkin displays that draw thousands of visitors to Kate Gould Park in Chatham every year—listed as one of America’s best towns for Halloween by Travel+Leisure. Celebrate the infamous ‘people’ unbelievable fashioned out of pumpkins, strike a pose with your favorite, then visit the celebrated shops on Main Street and #FallforChatham!

Sandwich Glass Museum PumpkinFest
Saturday, October 23
Be mesmerized by the shimmering, handblown glass pumpkins at the 10th annual outdoor pumpkin fest at one of Cape Cod’s Museum Trail destinations. This fanciful show and sale event showcases seasonally themed glass art you can illuminate around your home day or night for the perfect autumn décor.