Fall-Focused Events in Kennebunkport, Maine

Ghost, goblins, werewolves, oh my! As we enter into the official start of the spooky season, October in Kennebunk and Kennebunkport can get freakishly fun for all ages. This Halloween celebrate your fall trip to Maine by getting in on all the Halloween excitement and events with costume parties, a zombie dash, spooky treats, haunted tours, and more!

Halloween too spooky for ya? Don’t worry because this event calendar also includes fall festive activities outside of Halloween. Fall tours, fall fetes, farmers’ markets, pumpkin trolleys, and more.


October 15th, 2022 9 AM – 2 PM
Main Street, Kennebunk

Harvestfest is a fall event full of fun activities for all ages to enjoy. Activities will include a costume parade, book sale, live music, crafters and food, games, photobooth, a scavenger hunt, a nature walk, and more!

The Great Zombie Dash
October 28th, 2022 5:45 PM
Kennebunkport Conservation Trust

Kennebunkport Rec. and The Kennebunkport Conservation Trust are partnering together again to offer you an evening of community fun and adventure!

The goal will be to navigate the trail, overcome the obstacles, and make it out of the course with all of your lives (football flags) intact! Throughout the course, zombies will attempt to grab your flag as you attempt to avoid them. If you lose all of your flags you become “infected” and complete the course as an “infected’ person. However, if you complete the course with one or two of your lives intact, you will receive a raffle ticket per life and be entered into a drawing to win prizes!”

Halloween Costume Party
October 28th, 2022 9 PM -12 PM
Via Sophia by the Sea

“​​Wear your BEST costume to Via Sophia by the Sea’s spooky Halloween Costume Party on Friday, October 28 at the Rabbit Hole! The best costume will be competing for special prizes at the end of the night! Get spooky, enjoy great vibes, dance, and sip on some special Halloween cocktails throughout the night.”

All Souls’ Walk with the Brick Store Museum
October 29th, 2022 12 PM – 3 PM

The Brick Store Museum’s All Souls’ Walk began its annual Hallowmas season tradition in 2004, with a guided walk through neighboring Hope Cemetery. Now, in its 18th year, the event’s popularity continues! The All Souls’ Walk invites participants into Hope Cemetery and Woods, led by a knowledgeable tour guide, to “meet” the ghosts of Kennebunk’s past and learn about the lives of residents that came before us. Stories and experiences range from funny, to sad, to passionate, to mystifying. Not too spooky, it’s the perfect Halloween activity for the whole family. The tour lasts about 75 minutes and covers roughly a 1/2 mile through the cemetery. Learn more here.“

Spooky Teas and Tales
October 30th, 2022 4 PM – 6 PM
Kennebunkport Historical Society

“Join the Kennebunkport Historical Society for the first “spooky” themed tea and tales at the Historic White Columns property! This will include festive food, tea, and spooky stories of the Kennebunks!”

Stay tuned for more Halloween events added as information is released!

Shopping / Arts and Crafts

Fall Fete
October 15th, 2022 6 PM – 10 PM
Kennebunkport Historical Society

“Mingle inside with tastings and bites, enjoy live music by Beau Dalleo, join outside at one of our fire pits, cast your vote for your favorite scarecrow and enter to win some fabulous raffle prizes including a round of golf, a sailboat cruise, and more!”

Acrylic Painting on Canvas Workshops
Tuesdays 11:30 PM – 1:00 PM
River Tree Arts

“Are you looking for something fun and creative to try this fall? Join River Tree Arts for a relaxing afternoon of seaside painting! You will explore acrylic painting on canvas and learn some new techniques. River Tree Arts instructor Ms.Satsi will guide you in your art exploration process. Each student will work on their own canvas and table-top easel and leave with a work to be proud of. This workshop is for all levels and open to all ages.”

Kennebunk Farmers’ Market
Every Saturday 8 AM – 12:30 PM
Garden Street Municipal Lot

“Since 1993 the Kennebunk Farmers’ Market has been offering the finest in local foods at a convenient downtown location. Our market has grown every year and now features almost 40 local farmers and other vendors with a diverse offering of vegetables, fruits, flowers, eggs, meats, dairy products, herbs, baked goods, potted plants, and specialty products.”

Art Walk
October 18th + November 18th, 2022 5:30 PM – 9 PM
Live Cafe

“Join Live Cafe in celebrating all of the local artists on the third Friday of each month. Live Cafe will have local artists and artisans set -up on their lawn showcasing their work. Stop by to admire their creativity or take a piece home with you!”

Walks / Tours

Kennebunk Beach Walking Tour
October 1st + 8th, 2022 9 AM – 10:30 AM
Mother’s Beach

“This outdoor walking tour of Kennebunk’s Mothers Beach features eleven historic homes and an illustration of life at the beach in the early 20th Century. Every Saturday, tours depart from Trinity Chapel on Woodland Ave and last about 60 – 90 minutes. Less than a mile on sidewalks and flat terrain.”

Pumpkin Patch Trolley
Multiple times and dates

“Join Seashore Trolley Museum in beautiful Kennebunkport, Maine for the 24th Annual Pumpkin Patch Trolley.

Pumpkin Patch Trolley is the perfect fall event for all ages to enjoy! Board at the Visitors Center and take a trolley ride on the heritage railroad to The Pumpkin Patch. Each member in your group can select a pumpkin to take home, even the adults! Back at our Visitors Center, there will be fun activities to enjoy, including pumpkin painting, photo scavenger hunt, museum exploration, and more!”

Live Music

Dance Party with DJ Nate
October 3rd + 10th 8 PM – 11 PM
Old Vines Wine Bar

“An Old Vines tradition … and the most fun night of the week. Every Monday, Old Vines Wine Bar thanks the hardworking friends in the hospitality service industry with 50% off all food and drink, all night.Around 8pm, DJ Nate kicks off the dance party.
Whether you’re in the industry or not, come early for a quiet dinner and drinks, or come later for music and hijinks. Reservations suggested, but never required. All are welcome!”

Ocean Ave Band
October 5th, 2022 5:30 PM – 8:30 PM
Hurricane Restaurant

“Don and Lisa of Ocean Ave Band are psyched to be back at one of the Best Restaurants in all of the ‘Bunks- Hurricane Restaurant! From bluesy’ originals to cookin’ covers from Sinatra to Sting, Jobin to Adele, Muddy to Drake, come join us with Mark Gunter for the last event for the season!”

Bess Jacques and the Strays at The Rabbit Hole
October 6th, 2022 9 PM – 12 AM
Via Sophia by the Sea

“Join Bess Jacques and the Strays at the Rabbit Hole – a beautiful, cozy, and classy spot to hear jazz and vintage favorites while sipping a custom cocktail. With Bess Jacques on piano and vocals, and Darren Whitney on saxophone. Downstairs from the new and lovely restaurant, Via Sophia by the Sea.

Mid-Week Music Concert: Elvis
October 26th, 2022 7 PM -9 PM
October 30th, 2022 1 PM – 3 PM

“Join Dana Pearson, Mark Gunter, and Ron Breton for a concert featuring all Elvis music at the Town House School!

Chris Cyrus of Slack Tide
October 28th, 2022 7 PM -10 PM
Federal Jacks

“Spend your Friday evening waterside at Federal Jacks with Chris Cyrus, frontman for the local jam band Slack Tide, which is easily inspired by the Grateful Dead, Phish, and the 90’s ska movement.”

For more fall activities, check out our guide, ‘The Best of Fall in Kennebunkport’, including leaf peeping, beach walks, kayaking the Kennebunk River, and more.