Discover what's happening in Fall on Cape Cod

Provincetown Food & Wine Festival | November 5–8 (Approximately 50 minutes from Wequassett)

A celebration of Provincetown’s vibrant culinary scene, the Provincetown Food & Wine Festival brings together local chefs, restaurants, and wine enthusiasts for a flavorful long weekend. Highlights include the Grand Tasting at Town Hall, a Gallery Sip & Stroll, prix fixe dining at participating restaurants, and lively gatherings throughout town. It’s an inviting opportunity to experience Provincetown’s creative spirit through its food, wine, and culture.

Field of Honor Display | November 8–12 (Approximately 15 minutes from Wequassett)

Take a moment to honor the men and women who have served our country at the annual Field of Honor at Johnny Kelley Park in South Dennis. Part of a nationwide tribute to veterans, the display features rows of American flags waving in the autumn breeze. It’s a meaningful opportunity to reflect, remember, and recognize the individuals who have served.

Glassblowers’ Christmas at Sandwich Glass Museum | November 15–December 30 (Approximately 40 minutes from Wequassett)

Welcome the holiday season with an exhibition of beautifully handcrafted glass ornaments at the Sandwich Glass Museum. Featuring the work of glass artists from across the region and beyond, this annual display showcases an array of colorful, hand-blown creations. From whimsical figures to shimmering ornaments, it’s an inspiring stop for those seeking a distinctive holiday keepsake or a little seasonal inspiration.

Eastham’s Taste of Turnip Day | November 22 (Approximately 25 minutes from Wequassett)

A beloved Lower Cape tradition, Taste of Turnip Day celebrates one of the region’s most distinctive local harvests. Hosted by the Eastham Public Library, the event invites visitors to sample creative turnip-inspired dishes from more than 30 participating restaurants, alongside live entertainment, games, contests, and performances by the Wampanoag Nation Singers & Dancers. It’s a festive celebration of local flavor and community spirit.

Lighting of the Pilgrim Monument | November 25 (Approximately 50 minutes from Wequassett)

Mark the beginning of the holiday season in Provincetown at the annual lighting of the Pilgrim Monument. Taking place the evening before Thanksgiving, the celebration features music, local food, and festivities as 3,100 lights illuminate the historic monument. The display remains lit through January, making it a beautiful seasonal landmark to experience throughout the holidays.

Chatham Turkey Trot | November 26 (Approximately 10 minutes from Wequassett)

Start Thanksgiving morning with a Chatham tradition. The annual 5K Turkey Trot welcomes runners and walkers alike for a festive outing beginning at Oyster Pond at 8 a.m. Costumes and turkey hats are encouraged, and registration proceeds benefit the Lower Cape Outreach Council, supporting emergency food pantries throughout the Lower and Outer Cape. It’s a spirited way to begin the holiday before gathering around the table.

Truro Vineyards Holiday Market | November 27–28 (Approximately 40 minutes from Wequassett)

Welcome the holiday season with a visit to Truro Vineyards’ annual outdoor Holiday Market. Browse an array of handcrafted gifts and creations from local Cape Cod artists while enjoying seasonal refreshments and bites from the Crush Pad Food Truck. With local makers, festive shopping, and a beautiful vineyard setting, it’s a wonderful opportunity to find something special for the season.

Gardens Aglow at Heritage Museums & Gardens | Select Nights, November 27–December 27 (Approximately 40 minutes from Wequassett)

Step into a seasonal celebration at Heritage Museums & Gardens, where the grounds come alive with miles of twinkling holiday lights. Families can enjoy visits with Santa, carousel rides, model train displays, marshmallow roasting, live entertainment, and other festive activities throughout the gardens. With illuminated pathways and seasonal touches around every corner, Gardens Aglow is a wonderful way to welcome the magic of the holidays on Cape Cod.