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Start your fall off right in Provincetown!

September marks the transition from summer to fall in Provincetown and the month is packed with excitement! Sporting events, fundraisers, car shows, festivals, auctions, and more fill this month with activities that embody the broad appeal Provincetown has for everyone who visits.
The Great Provincetown Schooner Regatta rings in September from September 3rd - 5th. A race from Gloucester to Provincetown on the 3rd brings many tall ships into harbor for their subsequent races on the 4th and 5th. Spectators have a number of options for watching the races, including seats on a racing ship, in a spectator boat, from the shore, or with the Truro Center for the Arts at Castle Hill who will follow the Regatta and allow participants to paint, sketch, or photograph the race and Cape Cod Bay from their boat.

For over three decades, the Provincetown Harbor Swim for Life and Paddler Flotilla has illustrated the community-minded and celebratory spirit that makes the Town so special. This sporting event synthesizes an appreciation for Provincetown Harbor, one of the largest natural harbors in the world and ecological keystone of the area, and brings a community-minded approach to health and well-being by raising money for AIDS, women’s health, and the community. Friday, September 6th features orientation for swimmers and paddlers as well as the Celebration of Life Concert at 8 p.m. at the Unitarian Universalists Meeting House. Saturday, September 7th features the swim itself, starting at 8 a.m. The Mermaid Brunch, which is open to the public, starts at 10 a.m. Awards will begin at 11 a.m. or after the last swimmer arrives.
Next up is the Afterglow Live Performance Arts Festival from September 10 - 14th. Host to both popular and up-and-coming stage artists, the festival captures the historically theatrical spirit of Provincetown by gathering progressive artists and appreciative audiences for a week of performance art.
September 12th - 15th is the NGPA’s Cape Cod Classic, an event celebrating and uniting gay pilots around the country. The event includes break-out sessions, a keynote address, a dinner banquet, and more! Whether you are hoping to network, celebrate, or enjoy the beauty of Provincetown, join the NGPA for their annual event.
2019 sees the Provincetown Library host its 4th annual Book Festival, a free literary event for all book lovers. The event opens on the night of September 13th with the announcement of the recipient of this year’s Rose Dorothea Award, given to an outstanding author from or inspired by the Cape. This year’s winner is Mark Doty, an American poet and memoirist best known for his work “My Alexandria.” Over the next two days, the Library lawn features a massive book sale, readings from local authors, and more.
The Yankee Lambda Antique Car Show will be held on September 14th at the Pilgrim Monument from 10 a.m. to 1 p.m. The parade down Commercial Street begins at 1:30 p.m. If you aren’t able to witness the majestic beauty of these antique cars during these hours, the club members are around town all weekend, offering plenty of opportunities to catch a glimpse of their prized vehicles.
This year’s Annual Harbor to the Bay Bike Ride will occur on Saturday, September 14th. This ride from Boston to Provincetown is held to promote community awareness around HIV/AIDS care services and to support the organizations who improve access to quality care. Riders gather beforehand for stretching and breakfast before riding out. A celebratory lunch is held Sunday morning in Provincetown.
TEDxProvincetown, the platform famous for providing a setting for local speakers of all sorts to share their story, vision, and lessons, returns to Provincetown for the second year on September 14th. The event features scientists, drag queens, artists, and other critical thinkers from many different walks of life who will speak on a wide array of topics.
The 13th annual IWFFA Ptown Classic Women’s Flag Football Tournament comes to town September 14th - 16th, welcoming female participants who are already part of a team or looking to join one. Each night will feature parties and the Awards Party and Tournament Celebration will follow immediately after the championship game.
PAAM’s Annual Consignment Auction is held every September to commemorate deceased artists who lived, worked, or studied on Cape Cod. From September 6th - 21st, all works that will be up for auction will be displayed at the Museum as well as online. The auction will begin on September 21st at 7 p.m.
CASAS Animal Shelter hosts Pet Appreciation Week from September 22nd - 28th. Events include a photo contest, the Canine Games, a fish fry, and a pet parade on Saturday the 28th as well as parties at local venues. Participation in these events help this no-kill, all-volunteer shelter, continue to save lives and promote animal wellness so come out in support of a good cause.
Finally, the Provincetown Tennessee Williams Theater Festival closes out the month, running from September 26th - 29th. This year will feature plays both by Tennessee Williams and his Japanese friend and influencer, Yukio Mishima. The Festival seeks to promote Tennessee William’s connection to the Cape by celebrating his avant-garde spirit and cultural contributions to the artistic community through a series of invigorating performances each year.
About Provincetown
Provincetown, Massachusetts is a true melting pot. Located on the tip of Cape Cod, Provincetown boasts beautiful beaches, top-rated restaurants, art galleries, and charming shops. A top LGBTQ destination, this open-minded community celebrates individuality and freedom of expression. Provincetown has a rich creative history and is home to one of the oldest continuous art colonies in the country. The diverse population of artists, sailors, fisherman, authors, and more, makes Provincetown unique. From Carnival in August to Women’s Week in October and First Light at year’s end, Provincetown is thriving 365 days of the year.

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Provincetown Office of Tourism · 330 Commercial Street · Provincetown, MA 02657 · USA