Festivals & Events in Chatham
Experience our quintessential New England seaside village, renowned for its diverse array of events throughout the year. At Chatham Inn Relais & Châteaux, we embrace the local spirit, hosting and celebrating favorites such as Oktoberfest, Christmas by the Sea and First Night.
Explore the best things to do in Chatham and across Cape Cod for a truly memorable visit.
Filter By:
Oct30
Food & Drink
Falmouth Winter Farmer's Market
Check out the beloved market’s new location at Mullen Hall School.
Date: Every SundayTime: All DayLocation: Mullen Hall School
Oct30
Activities
Pumpkin People in the Park
Experience one of Cape Cod’s most beloved fall traditions as Pumpkin People in the Park transforms Ch...
Date: October 12 – 31Time: Recurring dailyLocation: Kate Gould Park
Nov12
Food & Drink
Caymus Vineyards Wine Dinner
Journey to Napa Valley for an evening highlighting the rich, distinctive wines of Caymus Vineyards. Settle ...
Date: November 12, 2026Time: 5:30 pm - 9:00 pmLocation: Cuvée Bistro
Dec10
Food & Drink
Stags' Leap Wine Dinner
Knock twice. Pour once. The Cellar Series concludes with Stags’ Leap Winery for an intimate, speakeas...
Date: December 10, 2026Time: 5:30 pm - 9:00 pmLocation: Cuvée Bistro
Dec11
Activities
Christmas by the Sea
A full weekend of small-town holiday traditions, shopping and family activities centered around Main Street...
Date: December 11 – 13Time: Recurring dailyLocation: Main Street and surrounding downtown Chatham, MA