Calendar of Events
Oct23Pumpkin People in the Park
Experience one of Cape Cod’s most beloved fall traditions as Pumpkin People in the Park transforms Chatham with whimsical, larger-than-life pumpkin displays created by local businesses, organizations and community members.
Date: October 12 – 31
Time: Recurring daily
Location: Kate Gould Park
Oct23Falmouth Winter Farmer's Market
Check out the beloved market’s new location at Mullen Hall School.
Date: Every Sunday
Time: All Day
Location: Mullen Hall School
Nov12Caymus Vineyards Wine Dinner
Journey to Napa Valley for an evening highlighting the rich, distinctive wines of Caymus Vineyards. Settle in for an intimate dinner where thoughtfully selected pours meet seasonal cuisine in the warm, elegant setting of Cuvée Bistro.
Date: November 12, 2026
Time: 5:30 pm - 9:00 pm
Location: Cuvée Bistro
Dec10Stags' Leap Wine Dinner
Knock twice. Pour once. The Cellar Series concludes with Stags’ Leap Winery for an intimate, speakeasy-inspired evening of celebrated Napa Valley wines and thoughtfully crafted cuisine.
Date: December 10, 2026
Time: 5:30 pm - 9:00 pm
Location: Cuvée Bistro
Dec11Christmas by the Sea
A full weekend of small-town holiday traditions, shopping and family activities centered around Main Street in Chatham. Some events require tickets; others are open to the public and free to attend.
Date: December 11 – 13
Time: Recurring daily
Location: Main Street and surrounding downtown Chatham, MA
