The best things to do in Chatham during the Winter

October 2024

Why Visit Chatham?

I can't think of another place I'd rather be - no matter the season - welcome to Chatham, MA! Our charming coastal town at the most Eastern point of Cape Cod (think: on the elbow) that offers a plethora of exciting activities for the whole family, including your furry friends! Whether you're seeking outdoor adventures or cozy indoor experiences, Chatham has something for everyone for your Cape Cod getaway in the Winter. In this post, we'll highlight the top 10 family and dog-friendly activities to enjoy during the winter season.

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Why visit Chatham in the Winter?

There are so many reasons! Unlike summer when Chatham's population rises to 30,000 people looking for the #capelife, the winter season offers visitors a much more relaxed environment. You will find most establishments are open, with less crowds, and no issues getting over the bridges. The weather can fluctuate ranging from bitter cold to downright mild so be sure to check the forecast before heading on your trip.

What should you bring with you on your trip to Chatham in the Winter?

Like mentioned, the weather can fluctuate in the Winter so double check that forecast before you leave - and be specific in searching Chatham's weather as it is common for several degree differences on Cape than the mainland. In any event, you can't go wrong bringing the following items:

10 fun family things to do in Chatham in the Winter (bring the dog, too!)

Now that we've set the stage, let's dive into 11 amazing family friendly things to do in Chatham during the winter.

1. Attend First Night Chatham:

Every year Chatham welcomes in the New in style! This is a great family-friendly, alcohol free, town-wide celebration of the arts with over 70 performances and events. Visitors can kick off the festivities by participating in the Town Photo at the Chatham Lighthouse, checking out a number of both indoor and outdoor performances and activities, and walk the Noise Parade on the way to see the Fireworks at Veterans Field. 

Take part in the Annual Town Photo at Lighthouse Beach

2. Visit the Monomoy National Wildlife Refuge:

Embark on a wildlife adventure at the Monomoy National Wildlife Refuge, a haven for nature enthusiasts. Take a guided tour to observe various bird species, seals, and other fascinating wildlife in their natural habitat.

Monomoy National Wildlife Refuge
U.S. Fish and Wildlife Services

3. Enjoy a Winter Hike at the Cape Cod Rail Trail:

Enjoy a scenic winter hike along the Cape Cod Rail Trail. This 22-mile trail offers breathtaking views of the Cape's natural beauty, and with its pet-friendly policy, your furry friend can enjoy the adventure too.

Cape Cod Rail Trail
AllTrails

4. Discover the Chatham Shark Center:

For an educational and interactive experience, visit the Chatham Shark Center. Learn about the fascinating world of sharks through exhibits, videos, and presentations suitable for all ages.

Atlantic White Shark Conservatory
Family Fun Shark Center

5. Indulge in Delicious Treats at the Chatham Candy Manor:

Treat your taste buds to a delightful experience at the Chatham Candy Manor. This family-owned candy store offers a wide variety of delectable treats, including homemade chocolates, fudge, and more. Be sure to try the Penuche! Don’t worry, they even have special treats for your furry friend!

Candy Manor
The Chatham Candy Manor

6. Take a Winter Boat Tour:

Embark on a winter boat tour and explore the scenic beauty of Chatham's coastline. Enjoy the breathtaking views of frozen marshes, lighthouses, and maybe even catch a glimpse of seals basking on the shores. Many boat tour operators welcome well-behaved dogs on board, so your furry friend can join in on the adventure.

Chatham Boat Tours
Outer Most Harbor Marina

7. Visit the Atwood House & Museum:

Step back in time and explore the rich history of Chatham at the Atwood House & Museum. This family-friendly museum offers exhibits and artifacts that showcase the town's maritime heritage. Well-behaved dogs on leashes are welcome to accompany you during your visit.

Chatham Historical Society
Atwood House Museum

8. Go Sledding at the Chatham Elementary School:

When the snow blankets the town, head over to the Chatham Elementary School for some exhilarating sledding fun. This family-friendly activity is perfect for kids and adults alike, and your dog can join in on the snowy excitement too!

9. Enjoy a Cozy Family Movie Night at the Orpheum Theater:

Wrap up your day of winter adventures with a cozy family movie night at the historic Orpheum Theater. This charming theater offers a selection of family-friendly movies, providing the perfect opportunity to relax and unwind with your loved ones.

Chatham Orpheum Theater
TripAdvisor

10. Explore the Chatham Lighthouse Beach:

Take a leisurely stroll along the picturesque Chatham Lighthouse Beach, where you and your family can enjoy the breathtaking views of the Atlantic Ocean. Make a visit to the “shack” in the dunes and don't forget to bring your furry friend along for a refreshing walk on the sandy shores.

Occupy Chatham South Beach shack
Wicked Local


Chatham, MA, is a winter wonderland filled with family and pet-friendly activities that will create lasting memories. From scenic beach walks to educational experiences and thrilling outdoor adventures, there's something for everyone in this charming coastal town. So book your stay at Pleasant Chatham Cape, pack your bags, bring your family, and don't forget your fur-baby, as Chatham awaits with open arms to provide you with an unforgettable winter getaway.

xo,

Jenn

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