(508) 432-5400 Reserve
Waterfront houses are reflected in a calm body of water, surrounded by autumn trees and grasses, evoking the vibrant spirit of Fall Festivals, with a small boat visible on the left side of the image.

Things to do in Fall on Cape Cod

Back

Experiences Overview

September - October
Call: (508) 432-5400
Several bowls filled with fresh oysters on the half shell are arranged on crushed ice, set on a wooden table—perfect for savoring at Fall Festivals.

Experience Cape Cod in Autumn

As autumn arrives on Cape Cod, towns and villages come alive with festivals celebrating the season and the people, flavors, traditions, and creativity that make the Cape so special. From local art and music to seasonal fare and time-honored traditions, there’s always something to discover. Explore beyond Wequassett and experience the many ways Cape Cod comes together to celebrate fall.

Discover what's happening in Fall on Cape Cod

September 11th – 13th – Eastham Windmill Weekend | Eastham (15-20 minute drive)

A celebration of the Eastham community with activities and events for all ages, including sand art, vehicle show, live music, food vendors, and beer and wine garden, road race and parade.

September 19th & 20th – Cranberry Arts & Music Festival | Harwich 

A beloved annual celebration featuring 150+ juried crafters, local food and drinks, kids’ activities, live music, and a spectacular Saturday night drone show.

September 19th & 20th – Bounty of the Sea, Truro Treasures | Truro (35-40 minute drive) 

Committed to the community of Truro with artists and flea markets, grape stomp, antique car show and treasure hunt.

September 20th – Grape Stomp | Truro (35-40 minute drive)

Celebrate the season with a festive day of grape stomping, food trucks, cocktails, wine, fresh oysters, and ice cream.

October 3rd – Mashpee October Fest | Mashpee (45 minute drive)

Spend the day exploring more than 50 local arts and crafts vendors, enjoying live entertainment, food trucks, and the festive Biergarten at Mashpee Commons Green.

October 4th – Love Local Fest | Hyannis (25-30 minute drive)

Brings nearly 100 Cape Cod artists, makers, and small businesses together at Hyannis Harbor for a day of local shopping, food and drinks, live music, kids’ activities, and community along the waterfront.

October 4th – Vinegrass Music Festival | Truro (35-40 minute drive)

Seven Americana and bluegrass bands across two stages, along with local wine and spirits, oysters, food trucks, and ice cream.

October 10th – Outermost Festival | Orleans (15 minute drive)

A fun day of roots, blues, Americana, and folk music to Nauset Beach, featuring live performances, local food and drinks, and a vibrant Cape Cod community atmosphere.

October 12th – 31st – Chatham Pumpkin People in the Park | Chatham (10 minute drive)

Creative and whimsical pumpkin displays crafted by local businesses, nonprofit organizations, and community members throughout Kate Gould Park.

October 10th & 12th  – Yarmouth Seaside Festival  | Yarmouth (25 minute drive) 

Brings the community together each Columbus Day weekend for a free, family-friendly celebration featuring more than 125 crafters, live music, children’s activities, nature shows, races, a beach bonfire, and a spectacular fireworks display.

October 17th & 18th – Wellfleet Oysterfest | Wellfleet (30-35 minute drive) 

This two-day family festival celebrates the town’s famous oysters, clams and shell fishing traditions bringing together locals and visitors alike for a weekend full of hometown flavor and big time fun!

October 17th – Oktoberfest in Chatham | Chatham (10 minute drive)

Head to downtown Chatham for a festive, family-friendly fall celebration featuring a kids’ zone, local food and beverages, entertainment, and seasonal activities.

November 27th – 21st Annual Chatham Turkey Trot | Chatham (10 minute drive)

Start Thanksgiving morning with a festive 5K run or walk through Chatham. Gather at Oyster Pond at 8 a.m. on November 27, where costumes and turkey hats are encouraged. Registration proceeds benefit the Lower Cape Outreach Council, supporting emergency food pantries throughout the Lower and Outer Cape.

White two-story house with blue shutters, blue front door, fall flowers, and pumpkins stacked in urns by the entrance—creating a warm, inviting atmosphere reminiscent of Fall Festivals. Plaque sign is visible on the right side near a small tree.
A close-up view of a large pile of small, round, bright red berries tightly packed together, capturing the vibrant spirit often seen at Fall Festivals.
A large group of cranberries floating in water on a cranberry bog, often seen during Fall Festivals, with trees and their reflection visible in the background under a clear blue sky.

Discover More Experiences