Very few vacation destinations match the hot pool parties and exciting nights Provincetown has to offer during the popular summer months. But it’s also not too early to make plans for an unforgettable fall getaway in America’s First Destination.
Locals and loyal visitors will tell you that Provincetown might be one of the nation’s best-kept secrets during September and October, a time when Ptown celebrates its “Second Summer.” In fact, this is the time when “Townies” say the best weather shines on the tip of the Cape.
When shops and hotels of most vacation destinations are locking their shutters and closing up for the winter, Provincetown is gearing up for its signature months.
It’s easy to revel in this time of year, as the warm sun mixes with brisk ocean breezes, stunning sunsets descend slowly into the sea, and night begin rolls in with a sea breeze to match the color of leaves preparing for early morning frost. Provincetown’s quirky shops, acclaimed 
restaurants and renowned art galleries are bustling, and the signature beaches remain a quintessential spot for rest, relaxation and fun. For flower lovers, it’s worth the trip alone to arrive in the midst of some of the most spectacular displays of dahlias during this time of year.
In addition to the beautiful weather and usual Ptown charm, the events of Second Summer have an intimate feel, and the town, still electric from nights of summer reveling, has 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 Sept. 7-10 with The Great Provincetown Schooner Regatta, a four-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. 12, 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 along with an unrivaled concert at the Unitarian Universalist Meeting Hall (UU), where local stars from town entertainment venues stage a talent show unlike any other as a celebration of life and a great weekend.
The Afterglow Festival begins on Sept. 14 and offers up an entire week of performance art by emerging as well as renowned artists. The National Gay Pilots Association land in town for the Cape Cod Classic, making the weekend of Sept. 18-20 time for a getaway to take advantage of the season. Celebrating works of an all time great, the acclaimed Tennessee Williams Theater Festival opens from Sept. 24-27, now in its 10th year and consistently wowing attendees with its creative takes on the work of one of America’s most beloved playwrights.
Polish up your gear and leather as October belongs in large part to LGBTQ events, kicking off with Mates Leather Weekend, Oct. 1-4. Columbus Day Weekend follows, reinvigorating Ptown’s party side leading into Women’s Week, Oct. 12-18, Provincetown Dance Festival, Oct. 23-24, and Fantasia Fair, Oct. 18-25, the longest-running annual event in the transgender world with show-stopping entertainment, workshops and more.
To put an exclamation point on a successful Second Summer, Ptown goes full-throttle for Halloween, with an eclectic schedule of spooky, sexy parties, street entertainment and events fit 
for every kind of angel, demon and daddy. Simply put, if you haven’t been to Halloween in Provincetown, 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 6-8.
Looking toward 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 the pilgrims landed at 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. Have your authentic feast in any one of many great fine dining restaurants.
After Thanksgiving, the Holly Folly arrives December 4-6. This popular three-day
LGBTQ festival kicks off the holiday season with a memorable lineup of events that includes the Gay Men’s Chorus and Shop Hop, a shopping event to vie for great prizes, taking advantage of Ptown’s shops and galleries’ major sales. Also on the schedule is the Inn Stroll and Drag Brunch, among others.
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. Over the years, fly and drive in visitors come to America’s First Destination to celebrate the new spirit of beginning in a place where it all began.
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.
