October is one of the best times to visit Cape Cod, thanks to two of the region’s most popular celebrations. The Outermost Roots & Blues Festival kicks things off on October 11–12, 2025, followed by the 25th annual Wellfleet OysterFest on October 18–19, 2025. Together these festivals showcase the heart of the Cape with incredible food, live music, and community spirit that draw visitors from across the country. If you are planning a fall getaway, these weekends offer the perfect mix of entertainment and coastal charm.
Wellfleet OysterFest
The Wellfleet OysterFest has grown into one of the most beloved gatherings in all of New England. What began in 2001 as a small community event is now a two-day celebration that attracts nearly 20,000 people to downtown Wellfleet. This year marks its 25th anniversary, and the festival promises to be bigger than ever.
The streets fill with energy as vendors set up along Main Street, offering everything from local art to Cape Cod crafts. Food stalls and wine and beer gardens provide plenty of ways to sample flavors from across the region, while live music adds to the festive atmosphere. For families, there is a dedicated area with games, crafts, and a bounce house, making the festival just as appealing for kids as it is for adults.
Of course, the star of the weekend is the oyster. Wellfleet oysters are world famous, and at OysterFest you can enjoy them freshly harvested by local farmers. Other shellfish from nearby waters are also served, and visitors can take part in culinary demonstrations to learn how to prepare them in creative ways. It is the perfect setting to savor the best of Cape Cod’s seafood culture while connecting with the people who bring it to life.
The Thrill of the Shuck-Off
No OysterFest would be complete without the legendary Oyster Shuck-Off. This competition has become the largest of its kind in the country and is one of the festival’s highlights. Competitors from near and far take the stage to battle for speed and precision as they crack open oysters at a lightning pace. The crowd cheers them on, creating an electric atmosphere as each contender fights for the title, cash prizes, and their name engraved on the Golden Oyster trophy. It is equal parts sport and spectacle, and for many, it is the most exciting moment of the weekend.
Outermost Roots & Blues Festival
Just a week before OysterFest, Nauset Beach sets the stage for the Outermost Roots & Blues Festival. Held October 11–12, this event celebrates the soulful sounds of roots, blues, folk, and Americana. National touring artists share the lineup with talented regional performers, filling the oceanfront air with music that feels as timeless as the Cape itself.
Beyond the music, the festival creates a full-day experience with food and drink vendors and a strong sense of community. You can spend the afternoon relaxing on the beach, listening to guitar riffs and bluesy vocals, then grab a bite or a drink as the sun sets over the Atlantic. The combination of live performances and the natural beauty of Nauset Beach makes this festival a standout part of Cape Cod’s fall calendar.
Book Your Stay with Pretty Picky Properties
If you are planning to join the festivities, finding the right place to stay will make your trip even better. At Pretty Picky Properties, we offer vacation rentals across Cape Cod that suit every style of traveler. Choose from luxury homes with high-end amenities, pet-friendly rentals so your four-legged family members can join the fun, or beachfront escapes that let you wake up steps from the ocean. Staying in one of our properties means you can relax in comfort after a day of music or oysters, with the space and convenience you need for an unforgettable trip.
Start Planning Your October Getaway
October is the time to be on Cape Cod, and these two festivals are proof of why. From the soulful performances at Nauset Beach during the Outermost Roots & Blues Festival to the food and fun of the Wellfleet OysterFest, you will experience the very best of the region in just two weekends. Start planning your stay now and book your Cape Cod rental with Pretty Picky Properties today!
