Cape Cod Events Calendar

Top Events & Festivals in Chatham, MA

Chatham is the quintessential New England seaside village, with its gorgeous beach, excellent dining, vibrant downtown and wonderful events throughout the year. Chatham Inn is proud to present and participate in the many activities that come to town, from golf outings and holiday events including Octoberfest, Christmas by the Sea and First Night, to our special Celebrity Food & Wine Series and charity events like Back to the Future Week. See what’s happening soon in Chatham and on Cape Cod…

October, 2019
Day(s) Date(s) Event
Fri-Thur October 18-31, 2019 Pumpkin People in the Park

Chatham Inn is happy to be participating once again in the annual Chatham Oktoberfest and the annual Pumpkin People in the Park display! Chatham area merchants prepare some incredibly creative pumpkin displays throughout Kate Gould Park. Chatham Inn won 1st Place in 2017—and we are looking for another win in 2019!
Sat October 26, 2019 Chatham Oktoberfest

We are pleased to be participating again in the annual Chatham Oktoberfest! Food, beverages, games, entertainment, and fun all day in Kate Gould Park in Chatham, just a few minute walk from Chatham Inn!
Saturday-Sunday October 19, 20, 2019 Wellfleet OysterFest

One of the largest events on the Cape, celebrating Wellfleet’s famous oysters. The two day festival combines food, art, music and fun! Tickets are $10pp.
November, 2019
Day(s) Date(s) Event
Saturday November 2, 2019 Cape Symphony "Bach and Forth"

Cape Symphony Orchestra presents an evening of the music of Johann Sebastian Bach, featuring grammy award nominates vocalist Skylark
Wednesday November 27, 2019 Annual Holiday Lighting of the Pilgrim Monument

Join this holiday tradition in Provincetown, the annual lighting of the Pilgrim Monument, which commemorates the Pilgrim’s first landing in the new world on November 11, 1620. Admission is free.
December, 2019
Day(s) Date(s) Event
Sunday December 1-30, 2019 Annual Glassblower's Christmas

See hundreds of unique glass ornaments on display at the Sandwich Glass Museum, hand crafted by the finest local artists.
Fri-Sun December 13-15, 2019 Chatham Christmas Stroll

Chatham Inn is pleased to once again be participating in the Chatham Christmas Stroll weekend and Historic Inn Tour! A full weekend of activities and fun is planned for our annual Christmas by the Sea, including the Friday night Christmas Tree lighting in downtown Chatham and the Historic Inn Tour on Saturday!
Tue December 31, 2019 New Year's Eve - First Night Chatham

Ring in the New Year at Chatham Inn!

Spend the day in Chatham with more than 70 musical performances and events throughout the town, then join us at our fine dining restaurant for our Chef’s annual 8-course New Year’s Eve wine pairing dinner. Complete the perfect New Year’s Eve with the annual Chatham fireworks over Stage Harbor.
January, 2020
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No Events this Month
February, 2020
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Fri-Sun February 14-16, 2020 Valentine's Weekend

Spend Valentine’s Day or weekend at The Most Romantic Hotel In New England! (2017, 2018 and 2019 TripAdvisor awards) and One of the 20 Most Romantic Hotels in the United States (USA Today.) Enjoy spa packages, special dinners, and romantic activities throughout the weekend. Book your romantic room or suite with a wood burning fireplace and your Valentine’s dinner in our beautiful restaurant by calling 508-945-9232.
March, 2020
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No Events this Month
April, 2020
Day(s) Date(s) Event
Sun April 12, 2020 Easter

Enjoy Spring on Cape Cod with a lovely Easter weekend stay, including Chef Christophe’s special Easter Dinner on Sunday, April 12.
May, 2020
Day(s) Date(s) Event
Sun May 10, 2020 Mother's Day

Treat Mom to a very special dinner at Chatham Wine Bar and Restaurant! Make your reservations early by calling 508-945-1468!
June, 2020
Day(s) Date(s) Event
No Events this Month
July, 2020
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No Events this Month
August, 2020
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No Events this Month
September, 2020
Day(s) Date(s) Event
No Events this Month

Some of our Notable Past Events

Celebrity Food & Wine Series Weekend: Patriot’s Day 
January 2017

Guests of Chatham Inn celebrated the release of Patriots Day, starring Mark Wahlberg, with a Friday night red carpet screening of the film at the Chatham Orpheum Theatre, and a Saturday night Wine Pairing Dinner at our restaurant, hosted by the film’s author Casey Sherman. Mr. Sherman, who also wrote The Finest Hours, attended the dinner, took photographs, autographed copies of his books, and answered questions about the film. Net proceeds benefitted the Arredondo Foundation.

Celebrity Food & Wine Series: Back to the Future Week
June 2016

Guests were able to get their picture taken with the DeLorean time machine—or even a ride in the car! There was an unforgettable ZD Wine Pairing Dinner with the stars of the original film, and a screening of Back to the Future with an exclusive Question and Answer session with Christopher Lloyd and Bob Gale.

Read More about Back to the Future Week at Chatham Inn.

Celebrity Food & Wine Series: Hell’s Kitchen with Rock Harper
January 2016

January 15-17th, 2016 was a full weekend of Food & Wine events. The weekend kicked off with a welcome cocktail party hosted by Dustin Moilanen of ZD Wines, Napa Valley, with guests relaxing and enjoying fine ZD wines and tapas fireside at the intimate Chatham Wine Bar. On Saturday, guests were treated to an exceptional six-course dinner prepared by Celebrity Chef Rock Harper, overall winner of Hell’s Kitchen. The dinner was expertly paired with premier ZD Wines (View Menu). Following dinner, David Magee, one of the top illusionists in the world, brought his sold-out Las Vegas show to the amazement and astonishment of guests!

Celebrity Food & Wine Series: Shooter McGavin
December 2015

“Shooter McGavin” himself, actor Christopher McDonald, hosted our first Celebrity Food & Wine Series event, quoting lines from Happy Gilmore while meeting and having fun with guests all weekend! The first wine pairing dinner was outstanding and took place during the annual Chatham Christmas Stroll weekend.