Top Things to Do in Provincetown, MA

Commercial Street Provincetown Massachusetts

Provincetown, located at the very tip of Cape Cod in Massachusetts, has spent the past few decades cultivating its reputation as a thriving arts community, a beacon of rich seafaring history, and a mecca for the LGBTQ community. Whether these aspects make it a top draw for you or not, there’s plenty to see and enjoy in this eclectic seaside town. Here are some of the not-to-be-missed activities you can look forward to on your visit.

Shopping & Dining on Commercial Street

This famed avenue stretches from the East End of the town all the way to the Provincetown Inn Seaside Resort and Conference Center in the west. Devote a morning or afternoon to strolling its length, stopping to sample the wares of the many bakeries and cafes that pop up along the way. If you’re an admirer of fine art, there are also a number of galleries to browse through, not to mention the Art Association & Museum in the East End. If your wallet is burning holes in your pocket, Commercial Street is also home to a myriad of locally owned shops and boutiques, offering everything from finely crafted jewelry to used books to Cape Cod souvenirs.

Pilgrim Monument Provincetown MA

Climbing the 252-foot-tall Pilgrim Monument

As the Pilgrims contributed greatly to the rich history of Massachusetts, it’s fitting that this monument should be located here at the farthest corner of the state. Those who are leery of kitsch need not fear—this isn’t a giant Pilgrim statue, but a stately building that offers unforgettable views of Cape Cod Bay and the surrounding towns. Make sure you leave enough time to explore the attached museum, which is both informative and entertaining.

Pedaling the Cape Cod National Seashore Bike Trails

Ready for some exercise? This area is home to some of the best bike trails in New England, as anyone who’s attempted the 5.45-mile Province Lands trail can attest. Be aware that this trail has some sharp turns, and is best enjoyed by cyclists of intermediate to advanced skill levels. Don’t forget to wear a helmet.

Whale Watching Provincetown MA

Whale Watching

This quintessential Cape pleasure will be an experience you’ll never forget, especially if the humpback whales are in an energetic mood on the day of your cruise. Whales aren’t all you can expect to see—keep your eyes peeled for gulls, dolphins, and seals as well, to name just a few. Be aware that these tours generally last for the better part of a day, and that the deep-sea swells can be rough—the whales aren’t just hanging around in the harbor, so those prone to motion sickness should either take the appropriate precautions or sit this one out.

Dune Tours Provincetown MA

Eating Sand on Art’s Dune Tours

Take in the Cape Cod National Seashore from a seat in one of these old-fashioned buggies, with an experienced guide to narrate your tour. For a truly exceptional outing, take the sunset tour, complete with dinner and a bonfire. If you enjoy water sports, there are “Dune and Water” packages available that include a kayak tour through the aquatic side of the park.

Taking the Mayflower Trolley Guided Tour

A ride on this trolley will tell you everything you wanted to know about this unique corner of the globe—and perhaps a few things you hadn’t thought to ask. The conductor will keep you entertained and amused throughout the journey, which departs from Town Hall and takes in all the essential downtown highlights. In season—from around Memorial Day weekend to mid-October—the trolley operates from 11 am to 5 pm, seven days a week. Private charter tours are also available.

Fishing Boat Provincetown MA

Chartering a Deep-Sea Fishing Boat

If you don’t think a day of fishing is quite the thing for you, this experience may invite you to reconsider your position. The moment the boat pulls out into open water, you’ll feel as if you’ve entered another world. The catch of the day is usually either tuna, bass, or bluefish, but that can vary based on the conditions, as well as on which charter outfit you choose. The boats place their emphasis on function rather than indulgence, so don’t expect high tea. In fact, most charters require you to bring your own food and drink—make sure you know what to expect when you book your trip.

Going to the Tea Dance at the Boatslip Resort

In high summer, every afternoon when the clock strikes four, the Boatslip goes into high gear with its hotter-than-hot outdoor dance party. The DJ knows how to keep the party rocking—you may find that the entire three hours have passed before you’ve had a chance to leave the dance floor.

Taking in a Drag Show

This activity has definite local color, but for that reason alone, it’s one you won’t want to miss. Not that it’s the only reason to take in a drag show while you’re here—the performers are legendary, with some carrying decades of hilarious history beneath their feathered boas. If you need help narrowing down your options, consider either the Crown & Anchor, The Art House, or the Governor Bradford Restaurant. All are beloved local institutions offering top-notch entertainment at reasonable (at least for the Cape) prices.

Whydah Pirate Museum Provincetown MA

Visiting the Whydah Pirate Museum Provincetown

Yes, you read that correctly—this is an honest-to-goodness pirate museum, featuring artifacts from a real-life shipwreck. The Whydah came to grief just off of Wellfleet in 1717, while carrying the plunder of some fifty ships. The surrounding story is mainly folklore, but the vessel was said to be commanded by Samuel Bellamy, who was bringing these stolen treasures to his true love when the Whydah ran into the storm that tragically ended its last voyage. Of the 146 souls aboard, only two survived, making this the deadliest wreck in Cape history. The museum strives to share this fascinating slice of pirating history with visitors, and is sure to be enjoyed by guests of all ages.

Long Point Lighthouse Provincetown MA

Enjoying the Views from Long Point Lighthouse and Race Point Lighthouse

What would a trip to the Cape be without a visit to a lighthouse or two? Long Point Light is fairly unassuming in stature—it’s merely a square white structure, measuring 35.5 feet in height—but it carries the distinction of marking the southwest edge of the entrance to the harbor. The light, as well as its corresponding oil house, are the only structures remaining on Long Point. The monument was listed on the National Historic Register in 1987.

Race Point Lighthouse is also listed on the National Register of Historic Places, and the site is considerably better furbished than its Long Point counterpart, with overnight accommodations available at either the Keeper’s House or the Whistle House. Visitors can even hold their wedding ceremonies here, with the glorious Cape beaches serving as a backdrop. Despite the modern updates that the property has seen throughout the years, when you visit the site, you’ll feel as if you’ve stepped backward through time.

Whether you indulge in all of the following activities or only one or two, there will always be some of that old Cape magic awaiting you here in “P-Town,” as the locals like to say. Best of all, if you don’t get to everything this time around, you’ll have an even better excuse to return as soon as possible. Enjoy the trip!

Dennis

Greetings from Provincetown at the Lands End and the tip of Cape Cod, Massachusetts. Cape Cod's #1 tourist destination, Even the PILGRIMS came here first! When I am your host, I will greet you upon arrival, show you to your rental, take a moment to go over a few things and to answer any questions, then leave you to enjoy your stay. My guest's total experience is of the utmost importance to me. I strive for 100% Satisfaction... I want every guest to have that just like home feeling. Come and Visit. Stay a day, a week or longer. See what Provincetown at the Lands End has in store for you !!! Warmly, Dennis L.

Related posts

Pilgrim Monument Provincetown MA

Getting to Know Provincetown, MA

While Provincetown (or “P-Town”) isn’t the easiest New England destination to access, the remote location only serves to increase its appeal. Situated... Read More

Commercial Street Provincetown MA

Top Places to Eat in Provincetown, MA

Located at the tip of Cape Cod, Provincetown was an old Portuguese fishing community in its early days. Its heritage began with... Read More

Join The Discussion

Search

December 2019

  • M
  • T
  • W
  • T
  • F
  • S
  • S
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
  • 29
  • 30
  • 31

January 2020

  • M
  • T
  • W
  • T
  • F
  • S
  • S
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
  • 11
  • 12
  • 13
  • 14
  • 15
  • 16
  • 17
  • 18
  • 19
  • 20
  • 21
  • 22
  • 23
  • 24
  • 25
  • 26
  • 27
  • 28
  • 29
  • 30
  • 31
0 Adults
0 Children
Pets
Size
Price
Amenities
Facilities

Compare listings

Compare