Wellfleet, Massachusetts Travel Guide

Shuck some oysters, square dance on the pier, and catch a drive-in movie in Wellfleet, Massachusetts, a city that's quieter than many of its New England neighbors (purposely so). The simultaneously sleepy and sophisticated Cape Cod town has all the ingredients of a great summer vacation. Browse our Wellfleet rentals and this detailed Wellfleet Travel Guide before visiting. Got any tips? Share them with us.

What to Do in Wellfleet, Massachusetts

Seaside and sentimental – that’s Wellfleet. Whether you’re watching the sun set over the horizon of Marconi Beach, reeling in a flounder on a rented sail boat, or studying an Indian artifact at the Wellfleet Historical Society Museum, you’ll feel free from any sort of schedule here. Replace that pile of to-do lists with a few days, or better yet a whole week, in this Cape Cod charmer.

Wellfleet Drive In Theater

Wellfleet Attractions

  • Wellfleet Drive-In Theater – it's one of the last of its kind in not only Cape Cod, but the country
  • Wellfleet Bay Wildlife Sanctuary – features songbirds, shorebirds, hummingbirds, butterflies, and year-round hiking trails
  • Town Pier – folks gather here to square dance on Wednesday evenings
  • Wellfleet Historical Society Museum – Wellfleet’s history is summed up well with the old photographs, clothes, nautical equipment, and intriguing whatnot, on display here
  • Chequessett Yacht & Golf Club – play a casual round of golf at this 9-hole course
  • Marconi Beach – fly a kite along the shore or go for a swim
  • Wellfleet Harbor – watch the boats glide past
  • Freshwater Ponds – take a calming Wellfleet fishing excursion to one of these
  • Cape Cod Bay – kayaking, boating, windsurfing, and of course swimming will make your day speed past

Book your Wellfleet vacation home today and you’ll be that much closer to these nostalgic and inspiring attractions. (Read more about Wellfleet Beaches.)

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What to See in Wellfleet

For people watching, take a stroll down Central Village, Wellfleet’s surprisingly bustling downtown. That’s hardly all Wellfleet has up its sleeves for sightseers, though.

Immerse yourself in an original play at the Wellfleet Harbor Actors’ Theater (WHAT). Or check out the Marconi Wireless Station – it’s not a wifi hotspot, but the remains of Guglielmo Marconi’s historic technological invention, which broadcasted the first wireless communication, “most cordial greetings from President Theodore.” Another sight worth stopping by (and listening out for) is the First Congregational Church’s Town Clock. But be ware. It’s not in time with Wellfleet and only makes sense to members of the Navy and those familiar with ship time. Take a peek into the First Congregational Church while you’re here. At more than one hundred and fifty years old, it’s just as enchanting as anything in Wellfleet. 

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Where to Shop and Eat in Wellfleet

Wellfleet OystersIt’s not called the “art gallery town” for nothing – while Wellfleet’s artistic offerings don’t match Provincetown’s, they come pretty close. You’ll find most of the city’s galleries in Central Village. If you consider yourself a collector or like to look at pretty and expensive things, visit the Cove Gallery. On the other hand, if you’re on a tight budget but want to find an eccentric gift for someone back home, the Left Bank Art Gallery is a good bet.

The Wellfleet Flea Market is a great hang-out spot for the family, as kids can interact on the playground while their parents shop for knick knacks. To turn some of your wardrobe into a consant reminder of Wellfleet, drop by Hannah. Once a private home, Hannah is now a high-end boutique featuring designer labels. 

Getting hungry? Chow down on Wellfleet’s famous oysters at the Wicked Oyster, MOBY Dicks, and Van Rensselaer’s Restaurant. If you like a little nightlife with your dinner, don’t miss the Beachcomber, one of Cape Cod’s most happening dance clubs.

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When to Visit Wellfleet

Summertime is vacation time in Wellfleet, so while you’ll share the view with thousands of fellow tourists, the weather will be perfect for swimming and all the attractions will be open. If you don’t want to miss out but don’t want to get lost in the crowd either, visit Wellfleet in balmy October and take part in Wellfleet OysterFest.

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What to Know About Wellfleet

Before you spend hours crafting the ideal itinerary, find out when various Wellfleet attractions are open and closed. Nothing will bum the family out more than venturing out to the Wellfleet Drive-In, only to discover it’s closed for the season.

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What to Bring to Your Wellfleet Rental

Sun block, a beach umbrella… your Wellfleet packing list can be as simple as you like, because after all, a Wellfleet vacation can be as simple as you like.

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Wellfleet’s Local Services

Watercraft rentals, bait and tackle supplies, beach accessories – it’s all here in Wellfleet. However, this town isn’t open year-round; if you’re visiting during the off-season, you'll have to do some hunting around for certain items.

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Getting to Wellfleet, Massachusetts

The Logan International Airport in Boston accepts most airlines. To get from Boston to Wellfleet, take MA-3 south and then get on MA-6. (Boston and Wellfleet are right across from each other, with Cape Cod Bay in between.) Chatham and Provincetown’s municipal airports are closer to Wellfleet, so if you can manage to catch a flight into one of these, you’re in for a much shorter drive!

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Why Wellfleet, MA Vacation Rentals?

Vacation Rentals.com has loads of Cape Cod vacation rentals, Wellfleet accounting for a lot of them. When choosing your Wellfleet accommodations, it’s really a no-brainer going with a private, affordable rental over a noisy, outrageously priced hotel room. Whether you’re planning a Wellfleet fishing trip or you’re hoping to take the city by storm, we’ve got a Wellfleet vacation rental perfect for your itinerary, group size, and budget!

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Photo by Britta Frahm.