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June 4th, 2021

Best Family Activities in Chatham


Another school year has come to an end and kudos to the kids, the parents and teachers because it has been quite the year! And now that things seem to be opening up, everyone is ready to get out there and get active again. And what better way to enjoy the outdoors and all the beauty that summer has to offer than a visit to Cape Cod with the whole family? So, pack your bags with swim trunks, towels and sunscreen and meet us in Chatham!



Whether you want to bring your own bikes or rent from one of several local spots, Chatham is a great place to kick off on your adventure! While Main Street can be a bit busy during the summer months once you get a little further out of downtown you can enjoy the picturesque scenery of blooming hydrangeas, charming cottages and of course stunning ocean views. And we always suggest hopping on the Cape Cod Rail Trail and making your way up to the National Seashore (now THOSE are some stunning landscape views).
When staying in Chatham you have a couple of great choices for bike rentals. There’s Hood Bikes, located directly on Main Street and they’ll drop off and pick up your bikes for you when you’re staying in town. And also, Wheelhouse Bike Co. Located a little farther up the street on Crowell Road.


The Orpheum

If you’re looking for a fun way to spend your evenings AND experience all the charm of small town life, we recommend going to the Chatham Orpheum movie theater. A much-missed institution in 2020 we are happy to announce they have reopened their doors for the 2021 season. An historic theater that first opened its doors in 1916, the local theater was a family destination all the way until 1987, where it eventually turned into a CVS. However, when CVS decided to relocate and the building was once again left vacant, a team of people worked together to raise the funds to reopen, and in 2011 they did just that!
Buy tickets online and enjoy JAWS in the summer as well as a wide collection of Indie movies and classic hits throughout the year!


The Shark Center

Speaking of ‘Jaws’…
With the resurgence of shark sightings over the last several years, Chatham has been put on the map (although we’re grateful not to have the same problems they did on Amity Island). Instead, even if you don’t spot a fin in the water, you can still get your fill of shark fun when you visit the Shark Center. Enjoy exhibits, videos and displays and learn what it is that has brought these big guys and gals back to the Cape!


The Chatham Anglers

It’s America’s pastime for a reason, and that’s because there’s nothing that screams ‘SUMMER!’ more than a baseball game in July. On Cape Cod we’re not shy when it comes to boasting about the Cape Cod Baseball League (ahem – the best amateur league in the country) and it is easily one of the best ways to spend your summer evening after a hot day at the beach. And not to brag, but the Chatham A’s play their home games just a short walk up the street from the Wayside Inn. And make sure to grab some Chatham A’s gear from the The Chatham Clothing Bar or Mahi Gold!


National Seashore

For those looking for a more ‘outdoorsy’ type of activity where you can take in the beauty of Cape Cod and some of the wildlife, it’s important to make sure you visit the National Seashore. Expanding through four of Cape Cod’s towns you can go as close as Eastham or as far up as Provincetown to enjoy beaches, ponds, lighthouses, and meadows. A personal favorite is the White Cedar Swamp Trail in Wellfleet, which is just over a mile long loop that allows for forest and beach views. Check out the National Park Service website for trails, maps, and tips on visiting this national park!





"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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"When I hear continental breakfast I don’t think of the outstanding breakfast they offer! Top notch breakfast, exquisite dinner, and the location is perfect! Excellent friendly housekeeping and quiet comfortable rooms! Couldn’t have been happier!"

Expedia Reviewer

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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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