Long weekend in Provincetown: Beaching, biking and best friends on the tip of Cape Cod
Long weekend in Provincetown: Beaching, biking and best friends on the tip of Cape Cod
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Long weekend in Provincetown: Beaching, biking and best friends on the tip of Cape Cod

🕒︎ 2025-10-21

Copyright cleveland.com

Long weekend in Provincetown: Beaching, biking and best friends on the tip of Cape Cod

PROVINCETOWN, Massachusetts – Before they settled in Plymouth, the Pilgrims first anchored in what would become Provincentown, on the northern tip of Cape Cod. It’s been a gathering place ever since. And last month, my favorite group of gatherers made its way to far eastern Massachusetts for a reunion six decades in the making. The 10 of us spent three nights in a historic house near the center of town and acted like we were 16 again (or maybe 56 – but who’s counting?) We danced, we drank, we talked, we walked, we worried, we shopped. Happy to say that no one cried (at least not that I know of). “We” were made up of five members of the Shaker Heights High School class of 1983, plus five spouses. These are my very best, longest-tenured friends, some of whom I don’t see nearly enough. We have done this before – at age 40, we traveled to Las Vegas for gambling, spa treatments and fine dining. A decade later, we gathered in New York City, for museums, Broadway and urban fun. This time, we settled on a more chill, beachfront destination. Why Provincetown? Eight of us had never been there. One couple vacations there every year – and we all were eager to find out why. It didn’t take long to figure it out. The town – with the Atlantic Ocean on one side and the Bay of Cape Cod on the other – is utterly charming, near beaches and bike paths, plenty of shopping, entertainment and places to eat. It’s also one of the country’s first and best-known gay-friendly vacation destinations, with an abundance of rainbow flags, weekend drag brunches and afternoon tea dances at the Boatslip. Ptown, as its affectionately known, has a year-round population of about 3,700, which swells to 60,000 during the summer. It’s typically packed during summer months, but we planned our trip for late September, as crowds wind down. We lucked out with terrific early fall weather, perfect for beach walks, bike rides and bonding. History and highlights Provincetown was founded in 1727, more than a century after the Pilgrims first landed here in November 1620. The Pilgrims stayed for just over a month, before relocating across the bay in what became known as Plymouth. While they were here, they created what they called the Mayflower Compact, which laid out the founding principles of self-government. It would become the hallmark of American political philosophy. In the center of Provincetown, the 252-foot-tall Pilgrim Monument, completed in 1910, pays tribute to these early pioneers. Climb the 116 steps to the top for a terrific display of the peninsula’s geography, with views of the town, the ocean and all the way to Boston on a clear day. The adjacent Provincetown Museum covers the community’s earliest history, from the Wampanoag people to the Pilgrims to the scores of Portuguese immigrants who arrived in the mid-1800s to work the whaling and fishing industries. Today, visitors still line up every morning at the Provincetown Portuguese Bakery for malassadas and other sweet treats. Starting in the early 20th century, Ptown evolved into an arty, bohemian destination, attracting writers and artists. Among the creatives who made the pilgrimage here: Tennessee Williams, Truman Capote, Norman Mailer, Jackson Pollock and numerous others. The combination of the welcoming Portuguese community and the growing artists’ enclave is largely credited with creating the foundation for America’s first gay-friendly vacation destination in the early 1900s. Fast forward more than a century and that welcoming, accepting atmosphere is still on display, no matter your age, race, gender or sexual orientation. Exploring the area Provincetown is surrounded by Cape Cod National Seashore, part of the National Park Service, with more than 40 miles of undeveloped coastal land, plus 40,000 acres of sand dunes, salt marshes, hiking and biking trails to explore. Our first morning in town, we walked to Herring Cove Beach, where one of my pals stripped down to his undies to fully sample the salt water. The rest of us were put off by the cold temperatures and the sign on the way to the sand that declared: “Warning – great white sharks hunt seals in the shallow water at this beach.” This beach is on the far end of the Cape Cod peninsula that curves back west, which means it’s a great place to view sunset. We returned later in the day with wine and fresh-made guacamole and cheered the colorful evening show. A bit farther from town is Race Point Beach, easily accessible on bike, with soft, dense sand that was a workout to walk through. Located here: the Race Point Light Station, one of 14 lighthouses on Cape Cod, and the historic Old Harbor Life-Saving Station, now a museum. Connecting Herring Cove and Race Point is the Province Lands Bike Trail, a 9-mile path, the first bike trail created on national park land. It was a terrific ride – through dunes, beech trees and bogs – the hills made easier with my rented e-bike. A group of us also walked across the breakwater, the rocky link that connects Provincetown and Long Point, the extreme tip of the peninsula, accessible at low tide. In the early 1800s, Long Point was home to a small settlement of fishermen who liked such easy access to the ocean. In the mid-1800s, however, they decided to move back to the main part of town by floating their houses across the harbor. Many of these historic “floater homes” are still standing in Ptown’s West End, identified by distinctive blue and white plaques. It’s a long, painstaking walk across the 1.2-mile-long breakwater, and we turned back before we reached the sand on the other side. To limber us up for all this exercise: a morning yin class on the living-room floor of our rental house, led by one of my traveling pals, a yoga teacher in real life. We stretched until our aging bodies complied. In town fun Activities in town included a climb to the top of the Pilgrim Monument, plenty of shopping and lots of people watching. Commercial Street is Ptown’s main drag, lined with art galleries, T-shirt shops, seafood shacks and ice cream parlors. One afternoon, half of us headed to the Boatslip, a Provincetown landmark, home to the afternoon tea dance – a tradition here since 1976 – a place to see and be seen. Tea dances got their start in the 1950s and ’60s in New York City and elsewhere, a way for clubs to throw off police, who often raided gay gatherings at night. Alas, we were a day early for the weekly Solid Gold Tea, featuring disco hits from the ’70s and ’80s. We made do with more modern house music, trying to channel those long-ago teen years when we used to sneak down to the Flats to party. That night, we enjoyed another Ptown tradition – a drag show at the Crown & Anchor, another local institution, where Anita Cocktail and a host of other dolled-up performers entertained a sold-out crowd. This trip, of course, was about more than the myriad activities on anyone’s to-do list. It was about celebrating friendships that have endured, and continue to endure, across numerous decades and many miles. No doubt, it would have been fun no matter where we ended up. But Provincetown, with its long history as a welcoming, festive gathering place, was the perfect spot for my favorite group of pilgrims. If you go: Provincetown, Massachusetts Getting there: Provincetown, at the tip of Cape Cod, is an 11 ½ hour drive from Cleveland. We flew to Boston and took the 90-minute Fast Ferry to Provincetown ($128 round-trip). The ferry, which departs from the Seaport, runs daily mid-May through mid-October and weekends only from mid-October through early December. Details: baystatecruisecompany.com Getting around: The town is very walkable and bike friendly. Depending on what you plan to do, you might not need a car. There are numerous bike shops in town, including Ptown Bikes, where we rented our wheels. Where to stay: Ptown is home to numerous inn and rental houses, none of them inexpensive. We spent three nights in the 7-bedroom Heritage House, which is rented through the Prince Albert Guesthouse. We paid about $1,500 a night, including taxes and cleaning fees. Where to eat: The seafood in this town is as fresh as it gets. On my plate for dinner: Cod at Bubala’s, lobster at the Canteen and lobster again at the Lobster Pot, a Provincetown landmark. We stocked up on snacks and other basics at the local Stop & Shop and enjoyed sweet treats from the Portuguese Bakery, Relish and ScottCakes.

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