This Is Massachusetts's Quirkiest Little Town
Artists, writers, fishers, whalers, Catholic Portuguese immigrants, and a thriving LGBTQ+ community are among the groups that call Provincetown home. The community has been welcoming arrivals from different backgrounds for over 400 years, starting with the Mayflower's landing in Provincetown Harbor in 1620. Today, the town runs year-round jazz and film festivals, hosts dozens of art galleries, and turns out the kind of waterfront seafood restaurants that keep the off-season busy. As a Cape Cod town, it also has some of the East Coast's best beaches and whale-watching spots. Travelers looking to explore the quirkiest corners of Massachusetts should not miss Provincetown.
The Country's Oldest Continuous Art Colony
Provincetown's art scene began in 1899, when American portrait painter Charles Hawthorne founded the Cape Cod School of Art there and started bringing students to paint the town's light and color. Since then, Provincetown has sustained an uninterrupted artistic community, and is generally credited as the country's oldest continuously operating art colony. While most visitors arrive in summer, galleries, exhibits, and events run year-round. Around 60 galleries stay open through the winter months, including Bowersock Gallery on Commercial Street, which focuses on contemporary and innovative work.
The Provincetown Art Association and Museum (PAAM), founded in 1914, is another anchor of the scene, with rotating exhibitions year-round. In February, the Provincetown Theater hosts the annual 24 Hour Play Festival, in which directors, playwrights, and actors have a single day to put together original plays for a public performance that night.
Annual Festivals & Events
The festival calendar runs through most of the year. In June, the Provincetown International Film Festival programs five days of American and international narratives and documentaries, with panel discussions and filmmaker events alongside screenings. Late June brings the Provincetown Portuguese Festival, which honors the town's Portuguese fishing heritage with live music, dancing, a fishing derby, a craft fair, and a blessing of the fleet.
August brings the Provincetown Jazz Festival, with musicians from around the country. Past performers have included New York's Finest Jazz Ensemble, the Afro Bop Alliance, and Lou Colombo. Book lovers should visit in September for the Provincetown Book Festival, which features guest speakers and authors, including Pulitzer Prize winners in recent years.
Beaches & Parks
There are miles of beach across Provincetown, with the Cape Cod National Seashore serving as the gateway to many of them. Herring Cove Beach and Race Point Beach are two of the most popular, both regularly rated among the best on the East Coast. Herring Cove Beach faces west over Cape Cod Bay, which makes it the go-to spot for sunsets. Race Point Beach, on the north-facing Atlantic side, has deeper water and is one of the best land-based whale-watching locations on the Cape. Race Point is also home to rolling dunes and historic landmarks like the Old Harbor Life-Saving Station Museum, an 1897 rescue station that was moved to Race Point in 1977.
Whale Watching
From April to October, humpback, fin, minke, and North Atlantic right whales are all regular presences off Provincetown. Race Point Beach offers decent land-based viewing, but a boat tour gives a much better shot at close encounters. Dolphin Fleet Whale Watch is the most established operator in town. Their three- to four-hour trips include a guided naturalist tour, upper and lower deck seating with a sundeck and bow viewing platform, and a galley with food and drinks. The company also guarantees sightings; if no whales are spotted, passengers receive a voucher for a future trip.
Culinary Scene
Provincetown's restaurant scene matches its arts scene, with most of the heavy hitters concentrated along Commercial Street. For views over Cape Cod Bay, Fanizzi's has been serving for roughly 25 years and runs a broad seafood menu including fish and chips, baked scallops, and Cajun seafood Alfredo.
For something more casual, The Squealing Pig serves pub food like burgers, sandwiches, and ceviche alongside an extensive craft beer list. Over on Bradford Street, Liz's Cafe Anybody's Bar is the go-to for breakfast, with indoor and outdoor seating and classic plates like eggs Benedict, scrambles, French toast, and pancakes.
Why Provincetown Works
Cape Cod has no shortage of summer destinations, but Provincetown is the one that holds up through the off-season. Between its four-century history, the country's oldest continuous art colony, a full festival calendar, and one of the best whale-watching coastlines on the East Coast, the town rewards more than a day trip. Step away from the typical Cape resort pattern and see what Provincetown has in store.
