14 ways to embrace Provincetown’s joyous quirkiness

Perched so far on the tip of Massachusetts’ Cape Cod that many call it the “end of the world,” Provincetown (known universally as P-town) has a long and complicated history as a safe harbor.

For thousands of years, the Indigenous Wampanoag (meaning People of the First Light) lived peacefully along these shores until European colonizers arrived, bringing disease and other misfortune in the early 1600s. In 1620, the Mayflower Pilgrims sought refuge here, followed by Portuguese fisherfolk and eventually artists, who spent the 20th century shaping the tiny enclave into a creative colony with progressive sensibilities.

Today, P-town's classic clapboard architecture can infer Kennedy-style Americana – yet its wholesome, Leave It to Beaver looks get subverted by the colorful townsfolk who define the place as much as weathered shingles. (We’re looking at you, local legend John Waters.) This is a world-famous haven for the LGBTIQ+ community – and as soon as Memorial Day comes, tens of thousands of visitors turn the town’s main drag into an all-inclusive, never-ending, four-month Pride parade.

Join vacationers crowding Commercial St between May and September, kick back on a windswept seashore in spring and fall, or cozy up inside a B&B to brave the intense winter. No matter who you are or when you visit, there’s always something exciting to do in Provincetown.

1. Enjoy the sand and surf on pristine Cape Code beaches

There’s no shortage of beaches in P-town. Step behind Commercial St’s harborside businesses, and you’ll find yourself on sandy expanses. If you're looking for a full-day affair, however, head to two oceanside escapes far from the main drag.

Perched on the Cape Cod National Seashore’s northernmost tip, Race Point Beach boasts miles of sandy dunes, wild crashing waves and seemingly endless sunlight. As night descends, wrap yourself in a blanket to admire the painting-worthy sunsets. If you visit in springtime, keep your eyes on the ocean: it’s possible to see whales breaching in the distance.

Just over a mile from Commercial St, Herring Cove Beach on Cape Cod Bay offers a gentler surf. On summer weekends, families build sandcastles near the parking lot while gay men head south to a slip of sand known as Boy Beach.

To access the queer section, enter at the bike-lined wood fence along Province Lands Rd, then hike toward the distant grass-topped dunes. On sunny days, brave sunbathers bask in their birthday suits, and the grass-covered dunes become a spot for cruising.

Plan your visit around low tide. If you miss your chance, expect to wade through waist-high water while returning to the road.

2. Dive into American history

Look toward the sky nearly anywhere in town, and you'll spot the 252ft-tall (77m-tall) Pilgrim Monument, which commemorates the landing of the Mayflower Pilgrims in America. (The Pilgrims spent five weeks in P-town in 1620 before sailing on to Plymouth Rock.) Built between 1907 and 1910, the tower is America's tallest all-granite structure. Climb its 116 steps for the reward of a breathtaking Cape Cod panorama.

After soaking up the views, head to the adjacent Provincetown Museum, which chronicles P-town’s maritime history through videos, artifacts and dioramas. A new wing of the museum, added in 2020, examines the Indigenous Wampanoag Nation, including how 17th-century encounters with European colonists led to their demise.

3. Get on two wheels: cycling is the best way to get around P-town

As soon as you get to the Cape’s tip, park your car and hop on a bike – for cycling is P-town’s go-to form of transportation. With two wheels, you can cruise through the town’s narrow streets without worrying about traffic congestion (or parking).

If you're willing to break a sweat, race to the Province Lands Bike Trail, starting at Herring Cove Beach, and glide over the changing landscape of white-sand dunes, scrubby pine forests and cranberry-filled bogs. The hilly 6.6-mile loop is a welcome respite from Commercial St’s constant hum. White-tailed deer and cottontail rabbits outnumber rowdy vacationers, and if you plan an early ride, you may get the trail to yourself. Break up the trip by stopping at the Province Lands Visitor Center, whose observation deck offers expansive views.

There are several spots to rent bikes in Provincetown, including Provincetown Bike Rentals and the Bike Shack. In peak season, reserve a set of wheels before arriving in town, as rentals can be hard to find during crowded weekends.

4. Gobble up local eats

Provincetown is packed with locally owned restaurants and cafes catering to various palates. Eat your way down Commercial St to sample local flavor.

Taste the town’s Portuguese history at the Provincetown Portuguese Bakery, dating back to 1900, and wash down one of their creamy pastéis de nata with a cold brew from Kohi Coffee Co. The Canteen is best for tacos and salads (including veggie-friendly options), while Relish’s deli sandwiches are great on the go. Place an order early and bring your treats to the beach.

When it comes to fine dining, Sal’s Place earns high marks. The elevated Italian fare here is served in a harborside house or outside on the beach, making for a truly romantic evening. Book a table well in advance.

For something low-key, stop by Provincetown Brewing Co. to sample a flight of the in-house brews with names like Asphalt Glitter and CrandaddySour  – which taste as good as they sound.

If you’re craving surf-y snacks, throw back a lobster roll at the Lobster Pot or order crab cakes at Mac’s Fish House. P-town was a fishing village long before it became a queer art colony, and you won’t find fresher seafood anywhere.

5. Go gallery hopping on Commercial St

Art seems to pour out of every door in P-town. Amble along the buzzy main thoroughfare, and you’ll find over 40 galleries chock-full of everything from painted landscapes to modern sculptures. The greatest concentration is on the East End – including William Scott Gallery, a contemporary outfit showing Edward Hopper–style scenes by revered local painter John Dowd.

Pop into galleries throughout the day, or join the throngs for Friday night’s Provincetown Gallery Stroll (late May to early October). The artwork might be expensive, but perusing the paintings is free.

Thanks to its endless vistas and dazzling light, P-town has attracted over a hundred year’s worth of artists to its shores. Jackson Pollock, Ann Packard, Paul Cadmus and Willem de Kooning are a few big names inspired by the town's picture-perfect backdrop. For a comprehensive look at P-town’s arty history, peek inside the Provincetown Art Association and Museum, established in 1914. Admission is free after 5pm on Fridays.

6. Take to the waters of Cape Cod Bay

Between April and October, Cape Cod Bay and Stellwagen Bank National Marine Sanctuary become an essential refuge for all types of whales, including humpbacks, minks and the endangered right whale. Join a boat tour to spot the gentle giants, along with gray seals, harbor seals and seabirds.

Dolphin Fleet Whale Watch hosts three-to-four-hour rides led by experienced naturalists. Bring a pair of binoculars for majestic creature close-ups, and consider popping a Dramamine to stomach rough waters.

For a laid-back seafaring experience, call on Dog Gone Sailing Charters. Lovably gruff Captain Rory brings 40-plus years of sailing experience – and plenty of stories about P-town’s bygone days – to a breezy boat ride around the tip of the Cape. Pack a small picnic, kick back with your beverage of choice and enjoy Cape Cod from a sailor’s point of view.

7. Shop local at one-of-a-kind boutiques

P-town’s unique shops are as vibrant as the characters strolling down Commercial St. Uber-queer clothing-and-art store Adam’s Nest sells graphic tees with an activist edge. Order a to-go tea at the Captain’s Daughters while admiring a hip assembly of apparel and home goods.

Full Kit Gear is a fetish-forward spot for men’s, um, clothes, while Toys of Eros is popular for its sex-positive treats and adult-toy museum. If you’re searching for beach reads by local scribes, hunt the shelves at East End Books for Mary Oliver’s poems and Michael Cunningham’s prose (Land's End: A Walk in Provincetown is a must-read).

Perhaps more interesting than the shops are their owners – amiable and often chatty entrepreneurs who function as P-town’s caretakers. Stop in, say hello – and remember to be kind. You may bump into them on the dance floor later in the evening.

8. Find your tribe at one of P-town’s countless themed weeks

The P-town experience changes drastically based on when you choose to visit. Themed weeks and events throughout the year attract particular members of the alphabet mafia, so if you plan on being social, find a theme that suits your style.

If you can think it, P-town hosts it. Single Women’s Weekend is for unattached lesbians and non-binary folks. Men of Color Weekend, along with a separate Womxn of Color Weekend, embraces the LGBTIQ+ BIPOC community.

July 4th week is popular with muscled party boys, while those who stick around for Bear Week get greeted by a slew of hair-forward gentlemen. There are weeks for families, the transgender community and even leather aficionados. Businesses and secondary events around town often cater to those visiting.

To see the Cape at its most colorful, visit for Carnival – a midsummer festival that’s equal parts Mardi Gras mayhem and Pride celebration. Make sure you bring an outfit to match the year's theme: the event brings in roughly 90,000 attendees, and you don’t want to feel left out of the fun.

9. Get rowdy at Tea Dance

When the clock strikes 4pm, a Pavlovian response takes over P-town: it’s time for Tea. This means one thing: gathering together on the Boatslip Resort’s spacious outdoor deck. Tea Dances became an LGBTIQ+ tradition in the 1960s when things like same-sex dancing and serving alcohol to known homosexuals were illegal. Calling gay gatherings “Tea Dances” was a clever way to disguise queer merriment from the authorities.

Today, P-town’s Tea Dance is a three-hour bacchanal during which people mingle while drinking anything aside from actual tea. Come dressed to impress: groups often attend in matching attire, ranging from baseball tees to drag regalia.

The tradition runs from May through September; a $10 cover charge applies (and is worth every cent). Arrive early to avoid long lines, particularly on holiday weekends. And bring cash to expedite the process.

10. Join the LGBTIQ+ community in partying all night

Cape Cod locals have a long history of partying hard. Atlantic House (usually just A-House) started slinging drinks back in 1798. Today, the complex – which includes a larger dance club and a men’s leather-and-Levi joint – is one of America’s oldest gay bars. Order a beer and toast the queer legends who came before you (Tennessee Williams was one), then move next door to cut a rug.

For something more salacious, drop by Purgatory and strip down to your skivvies. The basement club’s weekly underwear party gets so sweaty you’ll be happy not to be wearing clothes.

Throughout summer, a rotating roster of themed parties also takes place at Crown & Anchor, hosted by expert DJs with big-city pedigree.

Shipwreck Lounge, a cozy queer-forward cocktail spot, is a welcome respite from the thump of loud music. Take a seat by the roaring fireplace to unwind with a nightcap.

No matter where you end up, all roads lead to Spiritus. This late-night pizza joint, open till 2am on weekends, is the go-to for post-party munchies.

11. Laugh till your belly hurts at a live performance

As the sun sets over P-town, the stage lights warm up. Waltz down Commercial St post-dinner to the sounds of buskers, piano bars and the distant laughter of audiences wafting through the air.

The historic Crown & Anchor hosts two of the town's bigwig drag artists. Dina Martina – a bedraggled chanteuse whose singing is as hilariously bad as her lipstick – is a summertime must-see, while comedienne-songstress Varla Jean Merman gives off manic Carol Burnett energy.

Across the street is Art House, known for Seth Rudetsky’s Broadway Concert Series, which draws some of the biggest names and best belters in showbiz to town. For smaller acts, including up-and-coming drag performers, cabaret singers and stand-up comics, grab a seat at the Post Office Cafe and Cabaret.

P-town denizens have been trodding the boards for over a century. In 1915, the formation of the Provincetown Players ushered in an American theater revolution by birthing the career of Eugene O’Neill. To catch a full-length play, snag a ticket to one of the chamber pieces at the Provincetown Theater, founded in 1963 (open May through early December).

12. Join Halloween’s fright fest

Autumn's crisp weather means thinner crowds – unless you're visiting for Halloween. During October’s final weekend, P-town heats up with haunted houses, costume parties, movie screenings and all-night fêtes.

The ghoulish gathering reaches its climax on Saturday, when visitors stalk Commercial St in Hallow’s Eve drag before making mischief at Boatslip’s late-afternoon Tea Dance. Afterward, head to A-House or Crown & Anchor to dance until the devil’s hour.

Halloween coincides with Spooky Bear Weekend, a themed get-together hosted by the Northeast Ursamen (a bear-centric LGBTIQ+ group) that features a market, dune tour and costume ball. Although the group caters to furry gay fellows, the vibe is “all are welcome.”

Get into the supernatural spirit by visiting Winthrop Cemetery, established in 1793, for a run-in with P-town’s oldest permanent residents.

13. Search for solitude at the Cape Cod National Seashore

Just beyond Provincetown, the Cape Cod National Seashore has a landscape of shifting coastal dunes that attracts nature lovers year-round. Between spring and autumn, hikers take the Dune Shack Trail – a sun-exposed 2.5-mile loop whipped by Atlantic winds and covered in sand.

The trail passes a series of primitive cottages (dune shacks) first built to house shipwrecked sailors, which became artist retreats in the 20th century. Playwright Eugene O’Neill described the area as "a grand place to be alone and undisturbed.” Bring sunscreen and proper footwear, as the sand gets blisteringly hot on sunny days.

If you want to see the dunes without putting in the miles, plan a trip with Art’s Dunes Tours. This off-roading expedition explores the seashore’s history and ecology while covering some of its most scenic locales. Try the sunset tour or dune-and-kayak tour for a unique look at Cape Cod’s wilderness.

14. Cozy up to enjoy Provincetown in winter

Winter in P-town is a far cry from the summer’s busy scene. Snow-white blankets cover the beach, fierce winds blow in from the bay and the ocean, and many Commercial St stores close for the season. It’s a time of year best suited for curling up next to a fire in one of the town’s many inns or hiking through barren dunes without spotting another soul.

December still draws crowds thanks to Commercial St’s month-long holiday market and the Christmas-themed Holly Folly weekend, but tourism winds down after New Year’s Eve. Make the most of the slow season by visiting spots usually overrun during summer. Mac's Fish House, Provincetown Brewing Co. and the little bar at A-House are a few gems that remain open year-round, and it’s still possible to catch live performances at Tin Pan Alley. Winter is also the best time to meet locals.

P-town’s population shrinks below 3000 in the cold season, and those who stay are a ragtag group of artists, fishers and small-business owners happy to extol the town’s virtues to anyone willing to listen.