September kicks off the fall-travel season — one of the best seasons of the year to take advantage of terrific travel values in great places. With the summertime crowds gone, travel becomes more affordable post-Labor Day. While Provincetown, Mass., is magical any time of the year, fall is a perfect time to visit the LGBT-centric town.
Crowds jam the quaint streets of Provincetown in July and August, P-Town’s high season. Every week there is a theme week, from the recent Carnival to Bear Week and Family Week. While summer is arguably the best time to visit, hotels can be expensive and have minimum-night stays. Restaurant reservations can also be hard to get and bars and clubs are packed.
From art galleries to live entertainment and fine dining, there is a lot to see and do after summer. For beach and nature lovers, Provincetown is nestled on Cape Cod, alongside the National Park Services National Seashore. There are picturesque bike paths and tours of the dunes. While the nights are cool, most September days are warm enough for the beach and the pool. A great resource to plan your trip is P-Town.org.
Provincetown excels with events to draw visitors after Labor Day. Coming up this fall is the Mates Leather Weekend XXI Sept. 28-Oct. 1. Women’s Week is Oct. 8-15, and Oct. 15-22 is Fantasia Fair, the longest-running event for transgender individuals in the world. Activities and special events include 50 workshops, a fashion show, cabaret show and two formal banquets.
Among the many charms of Provincetown is the hotel and guesthouse experience. Each property is as unique as this quaint town itself. There is the adults-only Boatslip Beach Club with outstanding views of Provincetown Harbor and a nightly tea dance. The White Wind Inn is a fabulous Victorian mansion with the best views of Commercial Street from the property’s porch. The Brass Key Provincetown is a complex of luxurious rooms among several houses. The hotel has a heated pool, hot tub and special events all year long. It’s a nice spot for a wedding. P-Town is also a great place for Airbnb, with unique cottages and rooms for rent.
If you plan to visit Provincetown, get ready to figure out the best way to get there. It is located on Cape Cod on the very tip of the island. Your visit can require a lot of detailed planning from Philadelphia. If you fly, there are two great options on American Airlines and Jet Blue from Philadelphia International Airport, with many daily, nonstops to Boston. Once in Boston, you can take either Boston Harbor Cruises or Bay State Cruises and their fast ferries to Provincetown.
Schedules can be tricky, so be sure to coordinate your travel plans around the ferry schedule and leave yourself some extra time to get to the airport (which is just minutes away from the ferry arrival and departure locations).
You can also skip the ferry all together and fly on Cape Air. Amtrak is another good option but takes about five hours on the Acela. Driving is the option with the most flexibility but it does come with traffic, construction and other delays.