Discover the Charm of Provincetown, Massachusetts

Perched on the inner tip of Cape Cod’s curling peninsula, Provincetown (also called 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 brought disease and destruction in the early 1600s.

Then, in 1620, the Mayflower Pilgrims sought refuge here, followed by Portuguese fisherfolk and eventually artists, who spent the past century shaping the tiny enclave into a creative colony with city sensibilities.

Today, P-town’s classic clapboard architecture may infer Kennedy-style Americana, but its Leave It to Beaver looks get subverted by colorful townsfolk like local legend John Waters. This is a beloved haven for the LGBTIQ+ community, and when summer comes, thousands of visitors turn the town’s main drag into an all-inclusive Pride parade.

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

Enjoy Some Sand and Surf on P-town Beaches

There’s no shortage of beaches in P-town. Step behind Commercial Street’s harbor-side businesses, and you’ll find sandy expanses. However, if you’re looking for a full-day affair, head to two oceanside escapes far from the main drag.

Race Point Beach, perched on the Cape Cod National Seashore’s northernmost tip, boasts miles of sandy dunes, wild crashing waves, and seemingly endless sunlight. As night descends, wrap yourself in a blanket to admire the sunsets – there’s a reason landscape artists attempt to preserve them in paint.

If you visit in springtime, keep your eyes on the ocean – it’s possible to see whales breaching in the distance.

Herring Cove Beach, located just over a mile from Commercial Street, offers gentler surf on Cape Cod Bay. On summer weekends, families build sandcastles near the parking lot, while others enjoy the sun at a section known as Boy Beach.

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

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

Hit the High Seas in Cape Cod Bay

Between April and October, Cape Cod Bay and Stellwagen Bank National Marine Sanctuary become essential refuges 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 3-to-4-hour rides led by experienced naturalists. Bring a pair of binoculars for majestic creature close-ups, and consider popping a Dramamine for rough waters.

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

Cycling is the Best Way to Get Around P-town

Park your car and hop on a bike: cycling is P-town’s go-to form of transportation. Cape Cod traffic is notoriously hectic in summer, but with two wheels, you can cruise through town without worrying about congestion.

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 Street’s constant hum. White-tailed deer and cottontail rabbits outnumber rowdy vacationers; if you plan an early ride, you might just get the trail to yourself. Break up the trip by stopping at the Province Lands Visitor Center; check out the observation deck for expansive views.

There are several spots to rent bikes in Provincetown, including Provincetown Bike Rentals and the Bike Shack. Secure a set of wheels ahead of time, as rentals can be hard to find during peak weekends.

Go Gallery Hopping on Commercial Street

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

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

Thanks to its endless vistas and dazzling light, P-town has attracted over a century’s worth of artists. Jackson Pollock, Ann Packard, Paul Cadmus, and Willem de Kooning are just a few big names inspired by the town’s picture-perfect backdrop.

For a comprehensive look at P-town’s artistic history, peek inside the Provincetown Art Association and Museum, established in 1914. Admission is free on Fridays after 5pm.

Shop Local at Quirky Boutiques

P-town’s unique boutiques are as vibrant as the characters strolling down Commercial Street. Adam’s Nest – an uber-queer clothing-and-art store, sells graphic tees with an activist edge. Order a to-go tea at the Captain’s Daughters while admiring a trendy selection of apparel and home goods.

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

Perhaps more interesting than the shops are the owners. These friendly and often chatty entrepreneurs act as P-town’s caretakers. Stop in, say hello, and remember to engage. You may bump into them on the dance floor later that evening.

Find Your People at a Themed Week

The P-town experience shifts drastically based on when you choose to visit. Themed weeks and events throughout the year attract particular members of the LGBTIQ+ community, 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 designed for unattached lesbians and non-binary folks. Men of Color Weekend, along with a separate Womxn of Color Weekend, calls to the LGBTIQ+ BIPOC community.

July 4th week is popular with muscled party boys, and those who stick around for Bear Week get greeted by hair-happy gentlemen. There are designated weeks for families, the transgender community, and even leather lovers. The events around town often cater to visitors.

To see the Cape at its most colorful, consider visiting for Carnival – a midsummer festival that’s equal parts Mardi Gras mayhem and Pride celebration. Be sure to bring an outfit to match the year’s theme – the event draws roughly 90,000 attendees, and you won’t want to miss the fun.

Dive into American History

Look toward the sky nearly anywhere in town, and you’ll spot the 252-ft tall Pilgrim Monument, commemorating the first landing of the Mayflower Pilgrims in America. (The Pilgrims spent five weeks in P-town before sailing to Plymouth Rock in 1620).

This all-granite structure, built between 1907 and 1910, is America’s tallest. Climb its 116 steps for a breathtaking panorama of Cape Cod.

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 and the impact of 17th-century encounters with European colonists.

Get Rowdy at Tea Dance

When the clock strikes 4pm, a traditional response takes over P-town. It’s time for Tea, which signifies one thing – gathering together on the Boatslip Resort’s spacious outdoor deck. Tea Dances became an LGBTIQ+ tradition in the 1960s when same-sex dancing and serving alcohol to known homosexuals were restricted. Calling gay gatherings “Tea Dances” was a clever way to evade authorities.

Today, P-town’s Tea Dance is a three-hour celebration where people mingle while indulging in various drinks, aside from actual tea. Dress to impress – groups often attend in matching attire, ranging from baseball tees to extravagant drag outfits.

The tradition runs from May through September; cost is $5 from Monday to Wednesday and $10 from Thursday to Sunday. Arrive early to avoid long lines, especially on holiday weekends. Bring cash to expedite the process.

Party All Night with the LGBTIQ+ Community

Cape Cod locals have a long history of vibrant nightlife. Atlantic House, nicknamed A-House, has been serving drinks since 1798. Today, it’s one of America’s oldest gay bars and part of a complex that includes a larger dance club and a men’s leather-and-Levi establishment.

Raise a glass and toast to the queer legends who paved the way – Tennessee Williams was one – then move next door to dance the night away.

For a more risqué experience, drop by Purgatory and strip down to your underwear. The basement club’s weekly underwear party gets so sweaty you’ll be glad you opted for minimal clothing.

A rotating roster of themed parties takes place at Crown & Anchor throughout summer, hosted by expert DJs with big city credentials.

Shipwreck Lounge, a cozy queer-forward cocktail spot, provides a welcome respite from the loud music. Relax by the fireplace and unwind with a nightcap.

No matter where you choose to go, all roads lead to Spiritus. This late-night pizza joint, open until 2am on weekends, is the go-to for satisfying post-party cravings.

Gobble Up Local Grub

Provincetown is packed with locally-owned restaurants and cafes catering to diverse tastes. Eat your way down Commercial Street to sample the local flavor.

Experience the town’s Portuguese heritage at the Provincetown Portuguese Bakery, established in 1900, and enjoy a creamy pastel de nata with a cold brew from KōHI Coffee Co. The Canteen serves delicious tacos and salads (including vegetarian options), while Relish’s deli sandwiches are perfect for on-the-go meals. Place early orders and take your treats to the beach.

For fine dining, Sal’s Place is highly rated. The elevated Italian cuisine can be enjoyed in a harbor-side house or outdoors on the beach, making for a romantic dining experience. Reservations are recommended to secure a table.

If you prefer a laid-back atmosphere, stop by Provincetown Brewing Co. to sample a flight of local brews, featuring unique names like Asphalt Glitter and CrandaddySour.

For authentic seafood, indulge in a lobster roll at the Lobster Pot or savor crab cakes at Mac’s Fish House. P-town was a fishing village long before it became a queer art colony; you won’t find fresher seafood elsewhere.

Laugh Till Your Belly Hurts at a Live Performance

As the sun sets over P-town, the stage lights illuminate. Stroll down Commercial Street after dinner to the sounds of buskers, piano bars, and the distant laughter of audiences filling the air.

Crown & Anchor, a historic entertainment complex, hosts two of the town’s prominent drag artists. Dina Martina – a hilariously flawed chanteuse whose singing is as wonderfully bad as her lipstick – is a summertime favorite, while comedienne songstress Varla Jean Merman channels big Carol Burnett energy.

Across the street lies the Art House, renowned for Seth Rudetsky’s Broadway Concert Series, featuring some of the industry’s biggest talents. For more intimate acts, including up-and-coming drag performers, cabaret singers, and stand-up comics, find a seat at the Post Office Cafe and Cabaret.

P-town embraces its theatrical roots. In 1915, the formation of the Provincetown Players ushered in an American theater revolution by launching the career of Eugene O’Neill. To catch a full-length play, grab tickets to one of the chamber pieces at the Provincetown Theater, which operates from May through early December.

Search for Solitude at the Cape Cod National Seashore

Adventure just beyond Provincetown to the Cape Cod National Seashore, where a landscape of shifting coastal dunes beckons nature lovers year-round. Between spring and autumn, hikers venture along the Dune Shack Trail – a sun-exposed 2.5-mile loop, buffeted by Atlantic winds and covered in sand.

The trail winds past a series of primitive cottages (dune shacks) originally built to shelter shipwrecked sailors, then transformed into artist retreats in the 20th century. Playwright Eugene O’Neill described it as “a grand place to be alone and undisturbed.” Bring sunscreen and suitable footwear – the sand can get blisteringly hot on sunny days.

If you want to appreciate the dunes without hiking, plan a tour with Art’s Dunes Tours. This off-roading expedition explores the seashore’s history and ecology while showcasing some of its most scenic locales. Consider the sunset tour or dune-and-kayak tour for a unique perspective on Cape Cod’s wilderness.

Things to Do in Provincetown in the Winter

Winter in P-town offers a stark contrast to the bustling summer atmosphere. A blanket of snow covers the beach, and many Commercial Street shops close for the season. It’s an ideal time for curling up beside a fire in one of the town’s cozy inns or hiking through desolate dunes without encountering another soul.

December still attracts visitors thanks to Commercial Street’s month-long holiday market and the Christmas-themed Holly Folly weekend, but tourism declines after New Year’s Eve.

Maximize the slow season by visiting places typically overcrowded in warmer months. Mac’s Fish House, Provincetown Brewing Company, and the little bar at A-House remain open year-round. It’s also possible to catch live performances at Tin Pan Alley. Winter is the perfect opportunity to connect with locals.

P-town’s population shrinks below 3,000 in cold weather, and those who stay are a diverse blend of artists, fishers, and small business owners, eager to share the town’s many virtues with anyone who will listen.