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Fun Things to Do on Cape Cod in the Winter

Chilly weather makes for quiet, cozy visits to the Cape! With a significantly smaller population during the winter months, the area is very quiet, easy to navigate, and perfect for weekend getaways! There are plenty of things to keep visitors busy in the off-season. Be sure to take walks on the beach — there’s nothing like being the only person there! And definitely eat your way around the area. Not every restaurant will be open, but those that are will have no wait and, more often than not, they’ll have specials!

Here are a bunch of activities to keep you busy in the winter months, followed by a short list of cute and cozy spots to stay in while you enjoy them!

The Chatham Orpheum in Chatham.


The arts community is alive and well on Cape Cod! From art galleries to theater, almost every town on the Cape has one or the other — or both! If you find yourself in the town of Provincetown at the tip of the Cape, check out the Mosquito Story Slam, a live storytelling series where storytellers from the audience have 5 minutes to tell true, personal stories related to a theme. Or take in an art house film at the Waters Edge Cinema. Further down the Cape, you can enjoy one of the latest films with an adult beverage and tasty treat in hand at the beautifully renovated Chatham Orpheum Theater! Up-Cape, in Barnstable, you’ll find the Barnstable Comedy Club, where you find more than comedy — the oldest running, live community theater on Cape Cod and one of the oldest in America, features musicals and plays.


Featuring artwork from Cape Cod’s finest artists, past and present, is the Cape Cod Museum of Art located in Dennis. One town over, in West Yarmouth, is the Whydah Pirate Museum. Displaying artifacts recovered from an 18th-century vessel used for piracy and the slave trade just off the coast of Cape Cod, this museum is fun for mateys of all ages! Enjoy a live demonstration of glass blowing, and learn about the history of the oldest town on the Cape as well as view gorgeous glass collections at the Sandwich Glass Museum. And learn about one of the most famous families on the Cape at the John F. Kennedy Hyannis Museum where you can view thematic photographs, archival films, artifacts, text panels, and oral histories of John F. Kennedy and his family.

Cape Cod Beer in Hyannis.

Food & Drink Tours

There are many wonderful restaurants open throughout the year, but when you’re in a snacky kind of mood, head to the Cape Cod Potato Chips factory in Hyannis and take a free tour of their factory (and enjoy a free sample!) While you’re in Hyannis, stop into Cape Cod Beer, take a tour and raise a glass to sample their brewings. Keep on raising your glass as you head to the numerous wineries at Truro Vineyards and Cape Cod Winery for more tastings and tours!


If you’re looking for a fun indoor activity, try Ten Pin Eatery in Hyannis or the Orleans Bowling Center in Orleans. You will NOT strike out at either spot, as they both offer delicious fare, pub food and bbq, along with bowling and arcade areas.

Nauset Lighthouse in Eastham, the iconic landmark gracing Cape Cod Potato Chip Bags.


Lastly, if you have the time and want to see all of the Cape, consider visiting every lighthouse in the area. From Nobska Light in Falmouth, all the way to Race Point Lighthouse in Provincetown, the drive will take you through Hyannis, W. Barnstable, W. Dennis, Chatham, Eastham, and Truro.

Now that you know all the fun to be had in the winter on Cape Cod, you’re going to need a place to stay! Here are a list of cozy spots waiting to host your visit in the winter months!

1) Charming Farm Studio

2) Cozy Seaside Condo

3) 2 Bedroom Condo with Sweeping Views of Harbor

4) Luxury Beachfront Cottage

5) Newly Renovated Oyster Shack

6) Sweet 1 Bedroom Guest Cottage

About Jennie Sparrow

About Jennie Sparrow: I have been at WNAV for over three years and have loved every minute of it! A true Cape Codder, born and raised, my roots go all the way back to the Mayflower. I’m proud and humbled to call the Cape my home and love sharing my local knowledge with those visiting the area. My favorite pastime is going to the beach with my family and feeling the sun on my face and the sand between my toes!