Fall on Cape Cod is a magical time, filled with vibrant foliage, crisp seaside air, and charming events that celebrate the season. In addition to the breathtaking fall foliage, you can enjoy crisp ocean breezes and charming coastal towns. Whether you’re exploring the Outer Cape or venturing to the Upper Cape, there’s truly something for everyone.

Upper Cape:

Sandwich Glass Museum’s “Glass Pumpkin Patch – October 11-12, 2025:

Marvel at hundreds of hand-crafted glass pumpkins made by local artisans, browse, or purchase these stunning fall-themed decorations.

Mashpee Oktoberfest – October 4, 2025:

Held at Mashpee Commons, this event offers local craft vendors, German food and beer, live music, and fun activities like face painting and hayrides.

Sandwich Fest 2025 – October 4th, 2025

Head to Historic Sandwich Village for the 16th annual SandwichFest, a beloved fall tradition on Cape Cod. Enjoy a full day of shopping, local food, crafts, and family fun, plus live music during PorchFest in partnership with the Sandwich Arts Alliance.

Fall Fest Block Party (Mashpee) – October 11th, 2025

Celebrate the season at Mashpee Commons’ annual Fall Fest Block Party! Enjoy free, family-friendly activities with a festive, fall-inspired twist spread throughout the neighborhood. It’s the perfect way to spend a crisp autumn day on the Cape!

Mid Cape:

Yarmouth Seaside Festival – October 11-12, 2025:

This classic New England festival features a craft fair, live music, a parade, and fireworks by Seagull Beach. A family-friendly event that celebrates autumn on the Mid Cape.

Oktoberfest in Support of Dream Day (South Yarmouth) – October 4th

Celebrate Oktoberfest at Skull Island with local craft beers, food trucks, live music, and mini-golf fun for all ages. This family-friendly festival offers the perfect mix of seasonal flavor and entertainment. In addition, proceeds benefit Dream Day Cape Cod, supporting children with serious illnesses and their families.

Hyannis HyArts Shanties – October 10-12, 2025:

Stroll along Hyannis Harbor and explore the artist shanties filled with handmade goods, crafts, and seasonal treats. Overall, it’s a perfect spot for fall shopping and art lovers.

Lower Cape:

Chatham Oktoberfest – October 18, 2025:

Spend the day enjoying traditional German food, local brews, live music, and fun family activities. This event perfectly captures Chatham’s lively community spirit.

Outermost Roots and Blues Festival (Orleans) – October 11-12, 2025:

This multi-day music festival in Orleans showcases some of the best blues, roots, and folk musicians from across the region. Additionally, with performances set in a scenic location, festival-goers can enjoy great music, local food vendors, and a family-friendly atmosphere.

Brewster Historical Society Walking Tours – Various Dates in October 2025:

Discover Brewster’s rich history on a guided walking tour. Whether you join a spooky tour to hear tales of local ghosts and legends, or embark on a more traditional walking tour to learn about Brewster’s notable figures and historic landmarks.

Pumpkin People in the Park (Chatham) – October 10-31, 2025:

Lastly, stroll through Falmouth Village Green to see whimsical pumpkin people displays created by local businesses and residents, adding a festive touch to fall.

Outer Cape:

Wellfleet OysterFest – October 18-19, 2025:

This iconic festival celebrates the Outer Cape’s rich shellfish culture with oyster shucking contests, live music, local crafts, and delicious food vendors.

Provincetown Food & Wine Festival – November 6-9, 2025:

For wine lovers, this event offers wine tastings, gourmet food pairings, and cooking demonstrations. It’s a must for food and wine enthusiasts from all over New England.

Eastham Turnip Festival – November 22, 2025:

This quirky, beloved local event celebrates Eastham’s famous turnips. In fact, with themed games, contests, crafts, and tastings, there’s fun for all ages to enjoy.

Experience Cape Cod’s Fall Magic

Fall on Cape Cod is a special time. With its stunning fall foliage and vibrant community events, Cape Cod is an ideal place to call home. Whether you’re thinking of buying a second home, downsizing, or finding a larger space, there’s a perfect spot waiting for you here. And if you’re considering selling, fall’s natural beauty provides the perfect backdrop to showcase your home. Reach out to our team to explore your buying or selling options on the Cape.

Top Fall Events on the South Coast MA

Top Fall Events in Greater Boston