This Is Massachusetts's Quirkiest Little Town

At first glance, Provincetown may appear like a typical Cape Cod resort town. But if you look a little closer, you will find one of the most diverse communities in the country. Artists, writers, fishers, whalers, Catholic Portuguese immigrants, and a thriving LGBTQ+ community are a few of the groups that call this community home.

How did Provincetown become so diverse? The community has been welcoming individuals from different backgrounds for over 400 years. The Wampanoag and Nauset tribes were among the earliest settlers, living in the area long before the Pilgrims arrived in the 17th century. They were later followed by Catholic Portuguese immigrants drawn to the fishing industry. In the early 20th century, a wave of artists arrived, laying the foundation for the welcoming environment that attracted the LGBTQ+ community in the 1960s.

Today, the town continues to be home to jazz and film festivals, art galleries, and waterfront seafood restaurants that contribute to its lively reputation. 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 history dates back to 1916 when American portraitist Charles Hawthorne decided to work in town for the summer. Since his arrival, there has always been an artistic presence in the town. Although many travelers visit Provincetown in the summer months, there are art galleries, exhibits, and events that showcase the local artists year-round. During the winter, visitors will find around 60 art galleries open. Bowersock Gallery is a great one to check out, located along Commercial Street and serving as a gallery for some of the region’s most cutting-edge and contemporary art.

The Provincetown Art Association and Museum is another cultural landmark to check out, home to a series of exhibits that rotate year-round. In February, meanwhile, the town puts on the annual 24 Hour Play Festival. Directors, playwrights, and actors have just one day to prepare a play, attracting spectators from around the region to watch the final productions.

Annual Festivals & Events

In addition to the 24 Hour Play Festival, Provincetown has a wonderful calendar of events that keep the community engaged throughout the year. In June, visitors can attend the Provincetown International Film Festival, which features a five-day schedule of over 100 American and International narratives and documentaries. In addition to the film screenings, attendees can enjoy panel discussions and other special events with the filmmakers. Late June marks the Provincetown Portuguese Festival, which honors the town’s Portuguese heritage and fishing traditions through live music, dancing, a fishing derby, a craft fair, and more.

In August, the town celebrates the Provincetown Jazz Festival, which brings in jazz musicians from around the world to perform. Past performers have included New York's Finest Jazz Ensemble, the Afro Bop Alliance, and Lou Colombo. Book lovers should visit Provincetown in September for the annual Book Festival, where they can attend sessions with guest speakers and authors, including critically acclaimed writers and Pulitzer Prize winners.

Beaches & Parks

There are miles of beaches throughout Provincetown, with the Cape Cod National Seashore Park serving as a gateway to many of them. Herring Cove Beach and Race Point Beach are two popular beaches in the seashore park, both of which have been rated as some of the best beaches on the East Coast. Travelers wanting to catch a beautiful sunset should head to Herring Cove Beach, which is known for its iconic Atlantic Ocean sunsets. Race Point Beach, meanwhile, has deeper waters than some of its nearby neighbors, making it a great place to go whale watching. Other features along this beach include its rolling sand dunes and historic landmarks like the Old Harbor Life-Saving Station Museum, which dates back to 1897 as a historic maritime rescue station.

Whale Watching

From April through October, it is not uncommon to spot humpback, fin, and right whales off the Provincetown coastline. While travelers can certainly camp out at Race Point Beach to whale watch, joining a whale watching tour offers a better chance of seeing these majestic mammals up close. Dolphin Fleet Whale Watch is one of the most highly rated tour operators in Provincetown. Each three- to four-hour excursion includes a guided tour, a sundeck and bow viewing platform, seating on both the upper and lower decks, and a gallery offering food and drinks, ensuring that guests have a comfortable experience. The agency also guarantees whale sightings! In the rare case that none are spotted, passengers receive a voucher for a future trip.

Culinary Scene

Much like its art scene, Provincetown has a creative culinary scene, with many of its most popular restaurants located along Commercial Street. For panoramic views of Cape Cod Bay, travelers can eat at one of the seaside restaurants like Fanizzi’s. Operating in Provincetown for nearly 25 years, Fanizzi’s offers a variety of seafood dishes like fish and chips, baked scallops, and cajun seafood alfredo.

For a more casual, pub-style meal, consider dining at The Squealing Pig, which serves dishes like burgers, sandwiches, and ceviche, paired with an extensive craft beer menu. Nearby, on Bradford Street, visitors can fuel up for the day with a hearty breakfast from Liz's Cafe Anybody's Bar. A cozy cafe with indoor and outdoor seating, this spot offers classic breakfast favorites like eggs benedict, egg scrambles, french toast, and pancakes.

Final Thoughts

Cape Cod is one of those vacation destinations that checks all of the boxes. Not only does it have some of the region’s most pristine beaches, but it also is filled with art festivals, museums, and cozy restaurants that contribute to its quirky culture. Its status as a whale-watching destination is an added bonus on top of the rest of its features. So consider venturing away from the traditional resort destinations this year and explore what Provincetown has to offer.