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October 29th, 2021

Best Things to Do in Winter


Things to do in Chatham in the Winter 

Now, we know when people think of Cape Cod, they’re generally thinking of sunny days, sandy beaches, and a nice cold drink in their hand. Chances are, the Cape is pretty far from your mind when trying to decide on a good weekend getaway.  
But mayyybe we can change your mind? 
Because there is a certain beauty and charm in all New England towns in the winter, and Chatham is no exception. 
Here are our picks for some of our favorite winter activities in Chatham! 
1) See a movie at the Orpheum Theater on Main Street 

Ever since the Orpheum has reopened it has been a favorite of locals and visitors, and is it any wonder why with its small-town charm? Make sure to buy your tickets ahead of time so you don’t miss out! 

2) Go to the Beach 


No, we’re not crazy, we just suggest bundling up! Trust us, there aren't many things more stunning than an empty beach at sunrise, and if you’re in Chatham there are few spots that have a better view than Lighthouse Beach. Grab yourself a hot chocolate to-go and a pastry from Chatham Cookware and head on down to enjoy the view (with significantly fewer people than you’d find in the middle of July). 

3) Attend Local Events 

This will vary depending on what time of year you’d like to come, but we always suggest checking the Chatham Chamber of Commerce to see if there are any festivals or special events in town. For instance, in December, Chatham is famous for their Christmas Stroll weekend and ‘First Night’ on New Year’s Eve, where there are fireworks at midnight above Oyster Pond!  

4) Shopping on Main Street 


Believe it or not, many of our local shops DO stay open year-round. Of course, you’ll want to check their hours ahead of time (they are more limited in the winter) but it’s not uncommon to get a beautifully sunny day in February while you mosey through town. Make sure to check out our guide on our favorite shops on Main Street

5) Warm up with a cocktail 

One of the truly amazing things about Chatham, is you can find any kind of atmosphere you could want all within one street! Enjoy a couple beers while watching the game at the Squire, or dress up and enjoy a martini and delicious sushi at Blue Fins. Or, grab one of the specialty cocktails at the Wild Goose Tavern and sit by one of their fireplaces.  
Enjoy the magic of Chatham during its sleepy season and relax, we know you’ll enjoy! 

"The Wayside Inn is our little piece of heaven when we need to have a little bit of downtime. It is heaven on earth. The food is delicious and the staff extraordinary. They have become like a family to us. We would recommend The Wayside Inn to anyone looking for a special place to stay on Cape Cod. You will not be disappointed."

Patricia Abroderick, May 2022, Trip Advisor

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"The charm of the facility and the friendliness of the staff was amazing and we would definitely recommend this place and stay here again."

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