From festive village strolls to glamorous holiday markets, there's no shortage of upscale experiences to make your holiday getaway unforgettable. Here’s a selection of the season's most exclusive celebrations, each providing a taste of Cape Cod’s holiday magic.
Lighting of the Pilgrim Monument - Provincetown
Wednesday, November 27, 3 pm – 5:30 pm
Join the annual lighting of the Pilgrim Monument for a dazzling spectacle overlooking Provincetown. Enjoy live music from a DJ, festive drinks, and snacks at this free community event. At 5 p.m., the monument will light up in a display that illuminates the Cape’s coastal beauty.
The Canteen Holiday Market - Provincetown
Weekends from November 29 through December 29, 11 am – 5 pm
A must-visit for the discerning shopper, the Canteen Holiday Market features a collection of artisan stalls offering unique gifts and crafts by local vendors. Located on Commercial Street, this festive market is perfect for picking up hand-crafted treasures in a cozy, outdoor setting.
Lobster Pot Tree Lighting - Provincetown
Saturday, November 30, 5:30 pm
Experience one of Provincetown’s most cherished traditions: the lighting of the Lobster Pot Tree. Crafted from real lobster traps and adorned with bright lights, this coastal take on the Christmas tree brings a whimsical touch to Lopes Square.
Santa’s Workshops - Chatham Bars Inn
November 30 and December 7, 1 pm – 2:30 pm
Treat your little ones to a magical afternoon with Santa at Chatham Bars Inn, a luxurious seaside resort. The workshop includes crafts, treats, and a chance to meet Santa himself. Designed for children ages 4–10, this experience is available at $75 per child.
Holly Folly Weekend - Provincetown
December 6 – 8
As the nation’s original LGBTQ+ holiday celebration, Holly Folly offers an extraordinary mix of events, from the lively Jingle Bell Run (a Santa run in swimwear) and Champagne Brunch to drag bingo and holiday sing-alongs. This is a memorable way to celebrate the season with Provincetown’s vibrant community. Check ptown.org for a full schedule.
Brewster Windmill Lighting & Caroling - Drummer Boy Park, Brewster
December 6, 4 pm – 7 pm
Head to Brewster for a charming evening of holiday cheer. This free event includes the lighting of the town’s historic windmill, along with Christmas carols and complimentary cocoa.
Holiday Market and Tree Lighting - Wequassett Resort & Golf Club, Harwich
December 7, 11 am – 5 pm
Celebrate the season in style with a festive holiday market, tree lighting ceremony, and fireworks at the luxurious Wequassett Resort & Golf Club. Browse vendors’ offerings, sip hot cocoa, and soak in the sparkle. For the ultimate holiday escape, book the "Mrs. Claus Touch" package, which includes a room filled with seasonal delights.
Holiday Baking Classic - Wequassett Resort & Golf Club, Harwich
December 8, 11 am – 2 pm
Professional bakers are invited to compete in this holiday-themed baking contest, with top recipes earning a spot on the resort’s menu. It’s the perfect event for food lovers and anyone with a sweet tooth!
Brewster for the Holidays Family Party - Cape Cod Museum of Natural History, Brewster
December 8, 11 am – 1 pm
Enjoy family-friendly holiday fun with Santa photos, holiday music, and museum exploration. Free admission to this event makes it a perfect family outing for a day of festive cheer.
Chatham Christmas by the Sea Stroll - Chatham
December 13 – 15
This annual weekend celebration includes a holiday light parade, tree lighting, and entertainment throughout Chatham. Don’t miss the special movie screening and breakfast with Santa on December 14, making this a weekend full of traditional Cape Cod holiday warmth.
First Light Provincetown - New Year’s Celebration
December 30 – January 1
Ring in the New Year with nightly entertainment, a Polar Bear Plunge, and a dazzling fireworks display over MacMillan Pier. Provincetown’s First Light offers a mix of outdoor and indoor events, perfect for ushering in the new year Cape Cod-style. Visit ptown.org for full details.
First Night Chatham - New Year’s Eve Celebration
December 31, 12 pm – 10 pm
Join the festive spirit in Chatham with First Night, a family-friendly celebration featuring music, theater, fireworks, and more across the town’s venues. A $5–$30 First Night button provides access to most activities, with many outdoor events free to all.
Embrace the Holidays on Cape Cod
With each event steeped in Cape Cod’s unique charm and luxury, the holiday season here offers a distinctively memorable experience. From the grand lighting displays and holiday markets to intimate family gatherings and New Year’s festivities, Cape Cod is the place to savor the magic of the holidays in style.
