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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.

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A few people shopping at Falmouth Winter Farmer's Market
Sep27
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
Fresh Cape Cod cranberries at a Chatham farm stand
Sep27
Art

Cranberries: From Cape Cod to American Icon

Discover how the cranberry became an American icon through interactive exhibits that explore its deep roots...

Date: April 25, 2026 - October 18, 2026Time: Recurring dailyLocation: Heritage Museum & Gardens
Pumpkin People in the Park fall festival, Chatham, Cape Cod
Oct12
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
Oktoberfest beer steins near Chatham Inn, Cape Cod
Oct17
Food & Drink

Oktoberfest

Experience one of the Lower Cape’s favorite fall traditions at Chatham Oktoberfest, featuring festive...

Date: October 17Time: 11:00 AM – 5:00 PMLocation: Kate Gould Park
Caymus Cabernet Sauvignon from the wine list at Chatham Inn, Cape Cod.
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
Cabernet Sauvignon bottle and glass of red wine at Chatham Inn, Chatham, Massachusetts on Cape Cod.
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