A Weekend Traveler’s Guide to Provincetown

One of P-town’s most recognizable landmarks is the Pilgrim Monument and Provincetown Museum. / Photo by Scott W. Dunn/Getty Images

Among Provincetown’s many charms is its ability to endlessly reinvent itself. From its origins as a home for the Wampanoag and Nauset tribes to its 20th-century incarnation as an artists’ colony and a summer haven for the LGBQT+ community, the quirky town at the tip of Cape Cod never stops evolving. Even a quick trip reveals favorite places that have been recently reimagined and novelties waiting to be discovered. In fact, the only new thing to avoid is the recently opened police station.

Insta-worthy views of Race Point Lighthouse. / Photo by Betty Wiley

PLAY

For many people, P-town equals the beach, and that’s usually Race Point, Herring Cove, Long Point, and P-town Harbor. Nature lovers can spot cetaceans from the shoreline or choose among several whale watches, and a large network of bike paths makes P-town a cyclist’s dream. A new way to explore, however, is with Topless Tours Ptown, which offers off-road adventures in the dunes. Art aficionados, meanwhile, shouldn’t miss the Provincetown Art Association and Museum (which in 2016 became the second-largest repository of Edward Hopper’s work, after the Whitney) or the multimedia programming at the Fine Arts Work Center. The town’s most prominent edifice—the Pilgrim Monument and Provincetown Museum—offers a more majestic tribute to those intrepid puritans than Plymouth’s decidedly underwhelming rock, and is currently partnering with the Generations Project to show an exhibit chronicling the town’s LGBQT+ history. When it’s time to hoist a cocktail, revisit old standby the Gifford House, which recently underwent a complete makeover: Its nightlife venues include the Porch Bar, a refurbished Club Purgatory, and the Wilde, a theatrical speakeasy where shows include music, spoken word, and dramas written in a single day and performed as fresh as the drag queens you’ll find over at the Post Office Café and Cabaret.

Inside the world of John Derian. / Courtesy photo

SHOP

The dizzying array of retail options along Commercial Street ranges from the sublime to the ridiculous (see: the natural wonders at the Shell Shop, the designer finds at John Derian, and the unmentionables at Toys of Eros). Another must-visit is Coffey Men, which is back to constructing unique small-batch clothing on-site after a devastating fire. The sumptuous goods at Mauclere Leather are also designed and made by hand in P-town.

The pad see ew from Royal Thai. / Courtesy photo

EAT

P-town’s plethora of romantic restaurants include the Red Inn and the Mews, temporarily relocated to the Waterford Inn while they undergo a renovation, while newcomer Freeman’s serves up top-notch Mediterranean fare. Breakfast favorite Bagelhound is entering its second season, as is Royal Thai, an outpost of the Eastham eatery that’s located at Pilgrim House Inn. To equip yourself for a gourmet picnic by the sea, stop by Far Land Provisions for charcuterie, prepared foods, and sandwiches. And no trip to P-town is considered complete without a late-night slice at Spiritus Pizza.

A cozy guest room at the Land’s End Inn. / Courtesy photo

STAY

Situated atop Gull Hill, one of the highest points in the West End, the Land’s End Inn has been welcoming guests for nearly a century. Under new ownership since 2022, the rambling shingle-style beauty has updated its common areas and 18 rooms to include modern comforts and artistic flair (think purple walls with saffron leather sofas), but still retains its idiosyncratic, Hobbit-hole character and kooky flourishes—stained-glass windows, iron spiral staircases, and haute-granny décor. The rooms boast sweeping views of the harbor and dunes, and the inn’s location high above (but directly accessible to) Commercial Street removes it enough from the fray to make it a tranquil oasis. The whimsicality extends to the common areas, like the Chalice bar, which dispenses wine and beer from behind a pink Dutch door to be enjoyed on the lawn, while its serious side is reflected in owners Ed Macri and Trevor Mikula’s commitment to making the inn into a foundation that will support the local arts and LGBQT+ communities for generations to come.

GETTING THERE

You know the drill—after crossing the bridge, you’ll need to head allllll the way east on Route 6 until it narrows into a tiny strip of land with water on both sides. Or hop on the Provincetown fast ferry, which takes about an hour and a half from the Seaport.

First published in the print edition of the June 2024 issue with the headline, “Provincetown.”