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Your Ultimate Guide The Best Provincetown Events

By August 26, 2016January 21st, 2022No Comments

No matter what time of year you visit, the Provincetown events calendar is guaranteed to be full. Each and every month, there is at least one big festival, parade, or holiday celebration to attend. With so many exciting things to do in Provincetown all year long, it can be hard to decide what time of year is the best time to plan a trip to Provincetown. Luckily for you, we can help! Here is our ultimate guide to the best Provincetown events.

Provincetown and the surrounding area has so many things to do and we want to help you experience it all. Download our free vacation guide for a complete list of Provincetown events, landmarks, restaurants, attractions, outdoor activities, nightlife, events, and more!


New Year’s Day

Every year starts off with a bang in Provincetown. First Light Provincetown is an extended weekend celebration filled with special cocktails, dinners, and brunches, popular entertainment, special theme dance parties, lively community competitions and a weekend fireworks show!


Valentine’s Day Weekend

Provincetown is filled with cozy and secluded inns, candlelit restaurants, and luxurious spas, plus special Valentine’s themed balls and events. Provincetown is the perfect place for a Valentine’s weekend getaway.


Year Rounders Festival

After making it through the bitter New England winter, locals have every excuse to throw a party. Each March, Provincetown hosts the Year Rounders Festival to acknowledge the strength and fortitude it takes to live year-round in Provincetown. Locals and visitors alike celebrate at the Year Rounders Festival with great food, music, and art.

St. Patrick’s Day and the Out of Hibernation Ursamen

Celebrating the end of winter continues all March and St. Patrick’s Day is another great time to visit Provincetown. There are a number of family events around the holiday, as well as fun “Out of Hibernation” parties for adults.


Miss Gay Massachusetts US of A

The Miss Gay Massachusetts US of A pageant is exciting Provincetown event hosted in April. This pageant, a preliminary competition for the Miss Gay USofA national competition, includes interview, evening gown, and talent segments.

Patriots’ Day Weekend

Patriots’ Day is a unique Massachusetts holiday that commemorates the first battle of the American Revolutionary War. The weekend is celebrated in Provincetown and across the state with parades, festivals, re-enactments, and commemorative ceremonies.

Stomp! Gays for Patsy’s Annual Spring Hoedown

Gays for Patsy is a non-profit that hosts two-step, waltz, swing, and line dancing for the LGBTQ community in Boston, MA. But, for over 20 years, they have hosted a spring hoedown weekend in Provincetown. The event, in its 25th year this year, is open to everyone and features two dances, five workshops, and lots of other social events.


Run to the Top of the Pilgrim Monument

For nearly 10 years, the Cape Cod Firefighters and EMS Cancer Relief Fund has hosted an exciting fundraiser in Provincetown. The Run to the Top fundraiser features  walks to the top of the monument, silent auctions, raffles, food and drinks, live music, and activities for children. But, the main event is the competitive race up 116 stairs and 60 ramps to the top of the Pilgrim Monument!

Monumental Yard Sale

Twice a year, once in May and later in October, local businesses and Provincetown residents host a massive yard sale weekend that some say offers visitors the best shopping experience of the year. Attend the sale and you will find unique gifts, beautiful antiques, handmade art, and more!


Provincetown 10k

Wind your way through Commercial Street, past the Pilgrim Monument, and along the coast, as you compete in the Provincetown 10k every June!

Carnival of the Dogs

If you like to travel with your four-legged friends, plan a trip to Provincetown during the Carnival of the Dogs. This fun event is hosted at the Pilgrim Bark Park and hosts events and vendors that are perfect for you and your furry companions!


WorldFest is an annual celebration and international cultural festival. The weekend long event invites international workers, residents, and musicians to come to Provincetown and perform in a free concert.

Provincetown International Film Festival

If you are a film buff, make plans to visit Provincetown during its international film festival. The festival, hosted by the Provincetown Film Society, works to “make Provincetown the global destination for creative exploration in film.”

Provincetown Portuguese Festival & Blessing of the Fleet

One of the highlights of the summer, the Provincetown Portuguese Festival and Blessing of the Fleet celebrates Provincetown’s seafaring heritage with four days of music, dances, games, events, and more!


Independence Day

The 4th of July is always an exciting time to be in Provincetown. Commercial Street is lined with patriotic flags, the town hosts a festive parade, and fireworks always start at dusk over the Provincetown Harbor. There is no better place to watch the sky light up over the water from your view of the bay on Provincetown’s best beaches.

PAAM Annual Secret Garden Tour

If you’ve ever wanted to see some of Provincetown’s best-hidden gems, make plans to attend the Provincetown Art Association and Museum Secret Garden Tour. For 20 years, the PAAM has invited visitors to take a self-guided tour through Provincetown’s best private residences with stunning gardens.

Family Week

Now in its 22nd year, Provincetown hosts Family Week in conjunction with the Family Equality Council. Family Week is the largest annual gathering of LGBTQ families in the world and offers activities, events, and programming for all families.


Provincetown Jazz Festival 

Since 2005, the Provincetown Jazz Festival has brought Jazz musicians to Provincetown from across the United States, South America, Canada, the United Kingdom, Europe, and New Zealand to perform for a number of worthy causes. Proceeds from this annual event are donated to several nonprofits, including the Cape Conservatory CJazz Program

Carnival Week and Parade

Every year, Carnival Week is one of the largest outdoor celebrations in Massachusetts. For a week, Provincetown hosts themed parties, special events, and elaborate nightlife that all lead up to the annual Carnival Parade.


The Great Provincetown Schooner Regatta

The Great Provincetown Schooner Regatta is an educational sailing event that recognizes Provincetown’s maritime history and the beautiful natural resources in the area. This event works to promote public awareness of the role regattas and other seafaring vessels played in Provincetown’s history. The Great Provincetown Schooner Regatta celebration always begins on Labor Day and concludes with a regatta race on Thursday.


Fantasia Fair

Every October, Fantasia Fair hosts the longest-running annual conference in the transgender community. This event is a week-long celebration of gender diversity and includes formal banquets, over 60 workshops and seminars, special programs, and more.


Halloween in Provincetown is another week-long event filled with parties, parades, and more. As a chill creeps into the air, the heavy fog rolls in, and legends of pirates and abandoned lighthouses begin to swirl, Cape Cod transforms into frightening Halloween destination you have to see to believe!


Lighting of the Monument

The winter holiday season kicks off every year in Provincetown with the Lighting of the Monument. The Pilgrim Monument, visible from nearly every point in Provincetown, is decorated with festive lights that shine throughout the season.

Lighting of the Lobster Pot Tree 

Later in November, a second festive lighting that you won’t want to miss is the Lighting of the Lobster Pot Tree in Lopes Square. Each year, members of the Provincetown community build a Christmas tree out of more than 100 lobster pots, decorate it, and light it for the holiday season.


PGB Holly Folly Weekend

For three days in early December, Provincetown celebrates the the winter season with everything from  traditional carols ‘round the piano to a not so traditional Speedo run down Commercial Street. Holly Folly Weekend kick-starts the festive season with an eclectic assortment of holiday celebrations.

Experience the Best Provincetown Events with Us!

Nearly every weekend here in Provincetown, there is a holiday festival, a celebration or concert, or the reopening of a seasonal attraction. No matter what time of the year you stay at Admiral’s Landing, there is always something fun happening right outside our door! Our 1860’s historic and friendly bed and breakfast is centrally located just one block from Commercial Street. We invite you to come and enjoy our historic inn, friendly staff, luxurious guest rooms, and delicious homemade breakfast.

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