Provincetown: Plan for a Rejuvenating Second Summer

Provincetown, Mass. – For many people, Provincetown means a summer of beautiful beaches, hot pool parties and exciting nights – and it is certainly that. But it’s not too early to make plans for a rejuvenating fall getaway, and Provincetown might be of the nation’s best kept secrets during September and October, the ‘second summer’ months, as Ptown fans like to say.

While most vacation destinations are shuttering their windows and packing away the patio furniture, Provincetown, Mass., is rolling out a fresh season of diverse events that can only be found in this idyllic haven at the tip of Cape Cod.

Locals cherish this time of year, as warm sunshine mixes with cool ocean breezes, and long sunsets unfurl slowly into the sea. The town’s quaint shops, charming restaurants and renowned art galleries keep their doors open, and the award-winning beaches remain a picturesque spot for fun and relaxation.

In addition to the relaxed vibe, truly wonderful weather and usual Ptown charm, the real highlight of Second Summer is how the events take on an intimate, insiders feel. There’s still excitement in the air, but the throngs of July and August have dissipated, leaving a nice mix of sophisticates, adventurers and artistic souls to soak up the full scope of what Provincetown has to offer.

Second Summer’s slate of activities begins on Labor Day, a de facto farewell to summer that blends that season’s energy and seductive pleasures with fall’s grace. There are entertaining shows and dances throughout town, and the people watching remains first rate!

September 1-5 is The Great Provincetown Schooner Regatta, a five-day sailing event that brings the sailors to town and makes for an entertaining, edifying spectacle both on and off the water. Most of all, this event is a fitting tribute to the role that seafaring folk have played in Provincetown’s past and in the nation’s history.

On Saturday, Sept. 6, visitors can join in the Provincetown Harbor Swim for Life and Paddler Flotilla, a benefit for AIDS, Women’s Health and the Provincetown community. This event is considered one of the town’s quintessential traditions, and it anchors a weekend that is as fun as it is rewarding.

The Afterglow Festival begins on Sept. 8and offers up an entire week of performance art by emerging as well as renowned artists. This overlaps with Ptown’s 10 days of Art, featuring the many artists and galleries that call Provincetown home. The National Gay Pilots Association is also in town for the Cape Cod Classic, making the weekend of Sept. 12-14 an opportune time to sneak away and take advantage of the season. Other events continue through the remainder of September, highlighted by the Harbor to Bay Bike Ride on Sept. 20 and the acclaimed Tennessee Williams Theater Festival from Sept. 25-28, now in its ninth year and consistently wowing attendees with its creative takes on the work of one of America’s most beloved playwrights.

October belongs in large part to GLBT events, kicking off with Mates Leather Weekend, Oct. 2-5. Columbus Day Weekend follows, reinvigorating Ptown’s party side leading into Women’s Week, Oct. 13-19, Dance Festivals the 16-19 and 24-25, and then Fantasia Fair, Oct. 19-26, the longest-running annual event in the transgender world with show-stopping entertainment, workshops and more.

For most places, that would be a full month. But not Provincetown. As an uninhibited costume and dress-up destination, where people go to take off their everyday masks or don different ones, Provincetown is a natural fit for Halloween. But instead of coasting, Ptown goes full-throttle for Halloween, with a full schedule of spooky, sexy parties, parades and entertainment fit for every kind of angel, demon and daddy. Simply put, if you haven’t been to Halloween here, you haven’t been to Halloween, which also coincides with Spooky Bear Weekend, a burly event that’s devilishly fun. More manliness arrives in November, with Men’s weekend the 7-9 and Mr. New England Leather Nov. 21-23.

Looking towards the holiday season, why not spend Thanksgiving in the place where the Mayflower pilgrims first set foot in the New World nearly 400 years ago. That’s right, most people think of Plymouth Rock, but Ptown was the place, and Provincetown harbor is where the Mayflower Compact was drafted and adopted, leaving a legacy of independence that has only grown stronger for nearly 400 Thanksgivings since.

After Thanksgiving, the Holly Folly in December is a popular holiday celebration, and, before you know it, it’s time to make plans for New Year’s Eve in Provincetown, which, as you can imagine, is as wild and liberating as you want it to be.

For more information, please visit ptowntourism.com. And be sure to download the iPtown App, complete with a directory of town businesses and attractions, and a calendar of the year’s festivals events. Available on both iTunes and Google Play.