Chatham, Massachusetts Travel Guide

If you had to "paint" Chatham, you'd probably end up with a portrait of a seven-year-old boy, sitting on the edge of a dock, wearing an oversized fishing hat, holding a fishing rod, and patiently waiting for something to bite. But don't get the wrong idea; this small town’s no snooze. Chatham hangs off the mainland – it’s the tip of Cape Cod’s bony elbow – with water hugging it on three sides. Since its settlement in the 1600s, Chatham has claimed the hearts of countless beachgoers. If you require little more than sand and surf, rent a Chatham, MA vacation rental and read this guide to Chatham vacations while you’re at it. Got suggestions for our guide? Share them with us.

What to Do in Chatham, Massachusetts

Chatham Fishing

Things to Do on Chatham Bay and Beach

  • Fishing’s the best time waster in Chatham; read more about Chatham fishing here.
  • Take off on your sail boat at Pleasant Bay or Forest Beach.
  • Read a book and catch a tan on the calming shores of Nantucket Sound.
  • Give paddling a try on Pleasant Bay.
  • Watch the sun set over the Atlantic on Chatham Harbor.

Outdoor Activities in Chatham

  • The Play-a-Round Park was initially designed by famed designer Robert Leathers and although it’s been updated for today’s kids, it’s still as mesmerizing as ever, with unique distractions like a lighthouse and fishing net.
  • Play an easy, breezy 9-hole round of golf on the Chatham Seaside Links.
  • Find out what’s going on at Chase Park, Chatham’s favorite outdoor venue.
  • Bike through town without worrying about bad drivers. Chatham’s proud of its many biker-friendly paths!
  • Hike down scenic Seaside Trail.
  • Explore the pristine Monomoy Islands, just a ferry ride away, and observe rare birds and gray seals on their own turf.

Chatham Attractions

  • The Chatham Railroad Museum will transport you to the late 1800s; you can even walk through an old caboose.
  • The Old Atwood House Museum has been around since 1752, so it really is “old.” Journey through one of Chatham’s most historic homes and learn about the town’s beginnings.
  • Does the Old Atwood House pique your interest? There are more historic estates to explore, like the Mayo House
  • Get a pedicure or massage at Le Petite Day Spa.

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What to See in Chatham

From music to monuments, Chatham is full of wondrous sights and sounds. In the summer, Chatham features a band concert in Kate Could Park on Friday evenings. You don’t have to go out of your way to enjoy Chatham’s charm. Take a casual walk around town and stop by Chatham Light, a working lighthouse built in 1876. Or loiter around on the Chatham Fish Pier and watch fishing fleets unload their catches of the day. While here, take a picture with the Provider, a monument that pays homage to the Chatham fisherman (and fisherwoman, of course).

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Where to Shop and Eat in Chatham

Whether it’s fresh seafood or tasty French food you’re craving, Chatham's got it all. Here are our favorite Chatham eateries.

  • Breakaway Café – great spot for lunch
  • Chatham Squire – this restaurant bar is the top hangout spot in Chatham, and the baby back ribs are to die for
  • RooBar – it’s Chatham Squire’s only competition, with an appetizing menu and full bar
  • Vining’s Bistro – you may be in Chatham, but you’ll feel like you’re in another country at this worldly, yet surprisingly affordable café
  • Chatham Cookware – stock your Chatham vacation rental up with some goodies from this delightful deli
  • Marion’s Pie Shop – everything from clam pie to pumpkin pie is served here (between North Chatham and West Chatham)
  • Twenty-Eight Atlantic – this upscale restaurant is all about the ambience - enjoy breakfast, lunch, or dinner with a view of Pleasant Bay
  • Lazy Lobster – try the crab cakes
  • Sandi’s Diner – seafood’s great but sometimes you just want a burger

People don’t only come from near and far to eat; they also come to shop. Specifically, they go antiquing at Kahn Fine Antiques and Works of Art and fall in love with art at Nancy Cole’s Studio. Traveling with kids? Take them to the vintage Chatham Penny Candy Store.

If you promised you’d bring something back for friends and family, don’t miss out on the Chatham Jam and Jelly Shop and Chatham Cape Cod Specialties, where you can purchase a great gift basket full of the local flavors and charms of Chatham.

And finally, buy a new collar or graphic t-shirt for your pooch at the Chatham Beach Dog. Even if you don’t have a dog, this is a cute store to check out.

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When to Visit Chatham

Chatham is a summer destination – that’s when the weather’s prime for swimming and the city comes alive with festivals and events. Spring and fall are less crowded and more affordable times to visit, though. While it may be a little too cool for a jump in the bay, there’s still plenty to see and smell (the foliage is astounding) and enough restaurants and shops to keep you occupied for a whole week.

If you visit in December, make some rainy day plans; December is Chatham’s wettest month! So, while Chatham summer rentals are the standard, there are plenty exceptions.

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What to Know About Chatham

So, you’re ready to go fishing, huh? Well, you’re not the only one! Chatham is all about fishing. But there are many things to consider before you head out with your fishing pole. Anglers who plan to catch something in the ocean will have to go out about one hundred miles to do so legally. Don’t have your own boat? Don’t worry. Plenty of fishing charters are willing to chaperone you. Those who'd rather stick to land can try Goose Pond or Mill Pond. Just stop into Town Hall on your way because you’ll need a fishing license. Overfishing is a big problem in Cape Cod, so if you’re not playing by the rules, you’ll be found out.

As for getting around Chatham, it’s best to avoid driving. Main Street is overcrowded and there’s little parking available (unless you visit Chatham during the off-season). If you can’t go everywhere on foot, make sure to plan ahead.

Don’t stress out about whether or not Chatham locals will resent you for being on vacation while they're hard at work. Chatham residents are very friendly and welcoming.

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What to Bring to Your Chatham Beach Rental

Whether you’re on the beach or in a restaurant, don't give much thought to your outfit. The dress code in Chatham is super casual. But keep in mind that while the days are nice and warm, the evenings can get a little chilly. Pack along a light sweater or jacket.

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Chatham’s Local Services

Need a sailboat rental, directions to the Chatham Fish Pier, or fishing licenses? Chatham, Massachusetts, while small, provides lots of resources for its summer guests.

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Getting to Chatham, Massachusetts

Most likely, you’ll fly into the Barnstable Municipal Airport in Hyannis, but that’s just 20 minutes away from Chatham. International travelers will touch down in Boston’s Logan International Airport and then take a 90-minute or so drive to Chatham. There’s also the Chatham Municipal Airport, which accepts small and private planes. If you get lost on your way to your Chatham lodging, simply follow the signs on Route 28.

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Why Chatham, MA Vacation Rentals?

Private and spacious Chatham condos and vacation homes – at affordable rates – are available! As long as you stick to Chatham, MA vacation rentals, rather than hotels, you’ll save money and enjoy lots of space and amenities. We're positive you can find at least a few standouts among our many Chatham, MA summer rentals. So, whether you're looking for a property in North Chatham or West Chatham - we've got it waiting for you.

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