Why visit Cape Cod in the FALL?
Visiting Cape Cod in the fall is a magical experience, offering a peaceful and beautiful alternative to the bustling summer months. As the vibrant colors of autumn sweep across the peninsula, the crowds thin out, but the charm remains. The weather is often perfect for enjoying outdoor fall activities, from biking the scenic trails to exploring the quiet beaches.
This is a time when you can truly immerse yourself in the local culture, enjoying delicious seasonal food and unique festivals.
Our Brewster vacation rental is your perfect home base for a quiet Cape Cod getaway to experience the serene beauty that makes the Lower Cape so special.
Music & Arts Festivals
Harwich Cranberry Arts & Music Festival September 13-14, 2025
Celebrate the local harvest with this classic festival featuring live music, over 100 arts and crafts vendors, a Cranberry Arts tent, and a parade.
Provincetown Tennessee Williams Festival September 25-28, 2025
unique theatrical festival that honors the work of playwright Tennessee Williams, with performances held in various venues throughout the town.
Vinegrass Music Festival, Truro October 5, 2025
This one-day festival is a must for music lovers, showcasing a lineup of roots, Americana, and bluegrass artists to benefit a non-profit organization that provides scholarships to local music students.
Outermost Roots and Blues Festival & Outermost Friday, Orleans October 10-12, 2025
A celebration of roots and blues music with local artists and bands performing throughout the town, all in a lively and welcoming community atmosphere.
Pumpkin People in the Park, Chatham Mid-October to Halloween
One of the most charming and unique fall traditions on the Cape is Pumpkin People in the Park in Chatham. This delightful event transforms Kate Gould Park and the Main Street bandstand into a whimsical outdoor gallery, where local artists, families, and businesses create playful scenes using "pumpkin people" with pumpkin heads. As you stroll through town, you'll discover creative, often hilarious, displays that capture the community's spirit and artistic flair, offering a perfect photo opportunity and a sure sign that autumn has arrived.
Food & Drink Festivals
Wellfleet OysterFest, Wellfleet October 18-19, 2025
This is one of the Cape's most famous festivals, celebrating the town's legendary oysters with a weekend of delicious food, arts and crafts, and live music.
Cape Cod Brew Fest, Falmouth September 20, 2025
Sample an extensive selection of local and regional craft beers in this popular festival, complete with food trucks and live music.
Mashpee Oktoberfest, Mashpee October 4, 2025
Enjoy a traditional German-themed celebration with local food vendors, lively music, and, of course, a great selection of beers.
Oktoberfest in Chatham, Chatham October 18, 2025
This local Oktoberfest features live music, traditional German food, and plenty of beer to celebrate the fall season in a festive, community-focused setting.
Community & Family Fun
Eastham Windmill Weekend, Eastham September 5-7, 2025
A weekend of traditional fun centered around the historic Eastham Windmill. The festival includes a parade, craft fair, live music, and a road race.
Truro Treasures, Truro September 20-21, 2025
This community-wide event is a true local gem, featuring a festival parade, a craft fair, a wine tasting, and a number of fun events that celebrate the town's history and character.
Yarmouth Seaside Fest, Yarmouth October 11-13, 2025
A weekend full of family-friendly fun, including a craft fair, a bonfire, live music, a fireworks show, and a road race.
Sandwich Fest Street Fair, Sandwich October 4, 2025
This vibrant street fair showcases local food, art, and music, transforming the town center into a lively market with activities for all ages.
Sandwich Glass Museum's Annual PumpkinFest October 11-12, 2025
Sandwich Glass Museum's original and best outdoor festival fundraiser retail event of the year! Featuring glass pumpkins and other Autumn/Halloween themed handblown glass artwork from local and regional studio glass artists.
Mashpee Commons Halloween Parade, Mashpee October 25, 2025
A festive and family-friendly event where kids, adults and furry friends can show off their costumes and enjoy a parade through the Mashpee Commons.