Provincetown Events Calendar

Welcome to the Provincetown Business Guild calendar of events. There are many events hosted in Provincetown throughout the year, each with it’s own unique experience. Highlights include Yard Sale Weekends in May, Carnival in August, and Holly Folly in December – something for everyone!

If you have an event to include on our calendar, please fill out our Submit an Event form.

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May 2016

The Main Gallery at Castle Hill

May 5 @ 4:00 pm - October 28 @ 6:00 pm
Truro Center for the Arts at Castle Hill,
10 Meetinghouse Rd.
Truro, 02666
+ Google Map
Gallery

The Main Gallery at Castle Hill holds bi-weekly exhibitions.  Opening Receptions are on alternating Thursday from 4 - 6pm.  Light refreshments are served.  Come join us! Winter Clay Exhibition  May 5 - 12; Reception on May 12 Encaustic Juried Show: Mark of the Brush, juried by Christine McCarthy      and Gallery 1o: Encaustic Show May 23 - June 10; Opening Reception June 2; Closing Reception June 9 Summer Members Open Exhibition  June 14 - 24; Opening Reception June 16…

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Ruthie’s Boutique 50/50 Raffle

May 27 @ 8:00 am - September 5 @ 5:00 pm

WIN BIG! And help out Ruthie's Boutique,  Provincetown's charity thrift store,  at the same time. Our 50/50 Ruthie's Raffle will be going on all summer from May Day until Labor Day. Look for us around town selling raffle tickets.

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June 2016

2016 Broadway Series

June 25 @ 8:00 am - August 29 @ 5:00 pm
Crown & Anchor,
247 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Broadway's Finest Talent: Provincetown's Premiere Cabaret

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August 2016
$30

The Calamari Sisters SausageFest

August 23 @ 8:30 pm - August 25 @ 10:00 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Live at Sage! We are pleased to present the ONLY all-singing, all-dancing and all-cooking show in Provincetown. Back in Ptown for their third summer with their brand new show, Delphine and Carmela Calamari are bringing their 23rd Annual Italian SausageFest to Sage Inn. Whether you’re a sausage-lover or not, you’ll laugh until your sides ache. Get ready for a raucous good time and above all else, open wide ’cause here comes the sausage!

Find out more »
$15

Exploring Your Different Social Orientation

August 24 @ 10:00 am - 11:30 am
|Recurring Event (See all)
Meets every Wednesday between June 1 through August 31
Provincetown Public Library,
356 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

From an early age, gay boys are fundamentally different. We not only possess a different sexual orientation--we have a different social orientation. The traits of sensitivity, gentleness, kindness, non-violence, and cooperativeness enable us to play critically needed social functions. In this session, part of Provincetown's daily Gay Men of Wisdom Center, you'll explore your social orientation, and how it allows you to introduce collaboration into a hierarchical world.

Find out more »

Whiskey Wednesdays

August 24 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 7, 2016
The Pointe,
82 Bradford Street
Provincetown, 02657 United States
+ Google Map

  Join us at The Pointe for Whiskey Wednesdays weekly for distinctive whiskies with a story. Available by the glass, in our mixed drinks, or by the flight. Whether you are a connoisseur or novice we have something for all. Come and learn about cask strength, single malts, and whiskey vs. whisky.  

Find out more »
$15

A Guided Meditation through Your Gay Male Gifts

August 25 @ 10:00 am - 11:30 am
|Recurring Event (See all)
Meets every Thursday between June 2 through September 1
Provincetown Public Library,
356 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

An intellectual understanding of your gay male gifts gives you just one piece of the puzzle. When you feel it in your body and spirit, you gain a more profound awareness of how you serve an evolutionary function for humanity. In this guided meditation, part of Provincetown's daily Gay Men of Wisdom Center, you'll do energizing breathing while hearing summaries and affirmations of each gift. We seal each gift in with shared vocalizing, which creates a wordless connection to each other…

Find out more »
$30

BREAD AND PUPPET CIRCUS PERFORMANCE

August 26 @ 5:00 pm - 7:00 pm
Edgewood Farm,
3 Edgewood Way
Truro, 02666
+ Google Map

Castle Hill will present a performance by the Bread & Puppet Circus at Edgewood Farm on Friday, August 26 at 5pm. Tickets: $30. Come and join us for this magical event at our newly acquired property! Bread & Puppet Circus side show, in the pine forest BREAD & PUPPET CIRCUS WORKSHOP August 23 – 26, Tuesday – Friday $450 advanced registration required This unique workshop will involve participants in the creation and performance of two works:…

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Momma’s Boy

August 26 @ 10:00 pm
|Recurring Event (See all)
Weekly on the same day until September 3, 2016

Music by Billboard Magazine reporter and resident DJ David LaSalle every FRIDAY night!

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$300 - $350

Castle Hill Gala at Edgewood Farm

August 27 @ 6:00 pm - 10:00 pm
Edgewood Farm,
3 Edgewood Way
Truro, 02666
+ Google Map
Gala at Edgewood

The second annual Castle Hill Gala will celebrate the end of the summer at the bucolic Edgewood Farm. A delicious dinner, featuring  a bounty of local farm produce and seafood, will be served under a tent by Cosmos Catering.  The night will feature a dance floor and live music, so be sure to wear your dancing shoes.  Truro's star filled sky will provide the backdrop for lively conversations. Please come and enjoy the Castle Hill community at our prized location. …

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$30

The Calamari Sisters SausageFest

August 27 @ 8:30 pm - 10:00 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Live at Sage! We are pleased to present the ONLY all-singing, all-dancing and all-cooking show in Provincetown. Back in Ptown for their third summer with their brand new show, Delphine and Carmela Calamari are bringing their 23rd Annual Italian SausageFest to Sage Inn. Whether you’re a sausage-lover or not, you’ll laugh until your sides ache. Get ready for a raucous good time and above all else, open wide ’cause here comes the sausage!

Find out more »
Free

Piano Bar

August 27 @ 10:00 pm
|Recurring Event (See all)
Weekly on the same day until September 18, 2016
Porchbar Gifford House Inn Lobby,
9 Carver St
Provincetown, MA 02657 United States
+ Google Map

Billy Hough on piano and vocals No Cover

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$15

Surviving Provincetown and Making Authentic Connections

August 29 @ 10:00 am - 11:30 am
|Recurring Event (See all)
Meets on Mondays between June 6 and August 29 except July 4
Provincetown Public Library,
356 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

Provincetown can be both a magical and alienating place. We come seeking connections with other gay men, but often they either don't happen, or they don't satisfy us. In this interactive workshop, part of Provincetown's daily Gay Men of Wisdom Center, we'll ask, "What kinds of connections with gay men do we really want and need?" We'll explore The Seven Agreements, featured in Raymond Rigoglioso's book, Gay Men and The New Way Forward, through a creative group brainstorming exercise. You'll…

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Mellow Mondays @ Shipwreck

August 29 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 5, 2016
Shipwreck Lounge At The Brass Key,
10 Carver Street
Proivncetown , 02657
+ Google Map

  Bring a friend and join us every Monday night through labor day for a cocktail and for roasting marshmallows over our fire-pit.

Find out more »
$15

An Introduction to Your Gay Male Gifts

August 30 @ 10:00 am - 12:00 pm
|Recurring Event (See all)
Meets every Tuesday between May 31 through August 30 except July 5
Provincetown Public Library,
356 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

In this two-hour workshop, part of Provincetown's daily Gay Men of Wisdom Center, you'll take the 14 Distinct Gay Male Gifts Self-Assessment, which will help you understand which gay gifts you possess, and the extent to which you express them. We'll have discussions in small groups followed by a full group debrief. You'll complete the Distinct Gay Male Gifts Wheel, which will give you a visual picture of how you help humanity to evolve.

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Tiki Tuesdays @ Shipwreck

August 30 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 6, 2016
Shipwreck Lounge At The Brass Key,
10 Carver Street
Proivncetown , 02657
+ Google Map

 Ptown's own version of island time. Stop by Shipwreck Lounge to relax and have a cocktail every Tuesday night for our Tiki Tuesdays!

Find out more »
$30

The Calamari Sisters SausageFest

August 30 @ 8:30 pm - August 31 @ 10:00 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Live at Sage! We are pleased to present the ONLY all-singing, all-dancing and all-cooking show in Provincetown. Back in Ptown for their third summer with their brand new show, Delphine and Carmela Calamari are bringing their 23rd Annual Italian SausageFest to Sage Inn. Whether you’re a sausage-lover or not, you’ll laugh until your sides ache. Get ready for a raucous good time and above all else, open wide ’cause here comes the sausage!

Find out more »
$15

Exploring Your Different Social Orientation

August 31 @ 10:00 am - 11:30 am
|Recurring Event (See all)
Meets every Wednesday between June 1 through August 31
Provincetown Public Library,
356 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

From an early age, gay boys are fundamentally different. We not only possess a different sexual orientation--we have a different social orientation. The traits of sensitivity, gentleness, kindness, non-violence, and cooperativeness enable us to play critically needed social functions. In this session, part of Provincetown's daily Gay Men of Wisdom Center, you'll explore your social orientation, and how it allows you to introduce collaboration into a hierarchical world.

Find out more »

Whiskey Wednesdays

August 31 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 7, 2016
The Pointe,
82 Bradford Street
Provincetown, 02657 United States
+ Google Map

  Join us at The Pointe for Whiskey Wednesdays weekly for distinctive whiskies with a story. Available by the glass, in our mixed drinks, or by the flight. Whether you are a connoisseur or novice we have something for all. Come and learn about cask strength, single malts, and whiskey vs. whisky.  

Find out more »
September 2016
$15

A Guided Meditation through Your Gay Male Gifts

September 1 @ 10:00 am - 11:30 am
|Recurring Event (See all)
Meets every Thursday between June 2 through September 1
Provincetown Public Library,
356 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

An intellectual understanding of your gay male gifts gives you just one piece of the puzzle. When you feel it in your body and spirit, you gain a more profound awareness of how you serve an evolutionary function for humanity. In this guided meditation, part of Provincetown's daily Gay Men of Wisdom Center, you'll do energizing breathing while hearing summaries and affirmations of each gift. We seal each gift in with shared vocalizing, which creates a wordless connection to each other…

Find out more »
$30

The Calamari Sisters SausageFest

September 1 @ 8:30 pm - 10:00 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Live at Sage! We are pleased to present the ONLY all-singing, all-dancing and all-cooking show in Provincetown. Back in Ptown for their third summer with their brand new show, Delphine and Carmela Calamari are bringing their 23rd Annual Italian SausageFest to Sage Inn. Whether you’re a sausage-lover or not, you’ll laugh until your sides ache. Get ready for a raucous good time and above all else, open wide ’cause here comes the sausage!

Find out more »

Momma’s Boy

September 2 @ 10:00 pm
|Recurring Event (See all)
Weekly on the same day until September 3, 2016

Music by Billboard Magazine reporter and resident DJ David LaSalle every FRIDAY night!

Find out more »
$30

The Calamari Sisters SausageFest

September 3 @ 8:30 pm - September 4 @ 10:00 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Live at Sage! We are pleased to present the ONLY all-singing, all-dancing and all-cooking show in Provincetown. Back in Ptown for their third summer with their brand new show, Delphine and Carmela Calamari are bringing their 23rd Annual Italian SausageFest to Sage Inn. Whether you’re a sausage-lover or not, you’ll laugh until your sides ache. Get ready for a raucous good time and above all else, open wide ’cause here comes the sausage!

Find out more »
Free

Piano Bar

September 3 @ 10:00 pm
|Recurring Event (See all)
Weekly on the same day until September 18, 2016
Porchbar Gifford House Inn Lobby,
9 Carver St
Provincetown, MA 02657 United States
+ Google Map

Billy Hough on piano and vocals No Cover

Find out more »

Mellow Mondays @ Shipwreck

September 5 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 5, 2016
Shipwreck Lounge At The Brass Key,
10 Carver Street
Proivncetown , 02657
+ Google Map

  Bring a friend and join us every Monday night through labor day for a cocktail and for roasting marshmallows over our fire-pit.

Find out more »

Tiki Tuesdays @ Shipwreck

September 6 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 6, 2016
Shipwreck Lounge At The Brass Key,
10 Carver Street
Proivncetown , 02657
+ Google Map

 Ptown's own version of island time. Stop by Shipwreck Lounge to relax and have a cocktail every Tuesday night for our Tiki Tuesdays!

Find out more »

Whiskey Wednesdays

September 7 @ 5:00 pm - 9:00 pm
|Recurring Event (See all)
Weekly on the same day until September 7, 2016
The Pointe,
82 Bradford Street
Provincetown, 02657 United States
+ Google Map

  Join us at The Pointe for Whiskey Wednesdays weekly for distinctive whiskies with a story. Available by the glass, in our mixed drinks, or by the flight. Whether you are a connoisseur or novice we have something for all. Come and learn about cask strength, single malts, and whiskey vs. whisky.  

Find out more »
$30

Paint the Race

September 8 @ 12:00 pm - 3:00 pm
MacMillan Pier,
Provincetown , MA 02657 United States
+ Google Map

THE 13th ANNUAL CASTLE HILL “PAINT THE RACE” Aboard the Captain John Thursday, September 8, 2016 12:00 - 3:00pm Board from McMillan’s Pier, Provincetown $30 per person The 2016 Castle Hill “Paint the Race” on Thursday, September 8th invites artists and visitors from Cape Cod and the Northeast to participate in an extraordinary, unique opportunity to: “Paint the Race” from a whale watch boat during the Great Provincetown Schooner Regatta Race. Throughout the three hour cruise that is the highlight…

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Free

Piano Bar

September 10 @ 10:00 pm
|Recurring Event (See all)
Weekly on the same day until September 18, 2016
Porchbar Gifford House Inn Lobby,
9 Carver St
Provincetown, MA 02657 United States
+ Google Map

Billy Hough on piano and vocals No Cover

Find out more »

Poet Mark Doty Reads

September 15 @ 6:00 pm - 7:30 pm
Truro Center for the Arts at Castle Hill,
10 Meetinghouse Rd.
Truro, 02666
+ Google Map

Castle Hill is delighted to present an evening with poet Mark Doty. Mark Doty is the author of 12 books of poetry and prose he has explored the intensely personal—the illness and death of his lover from HIV—finding in individual stories a means to political and social engagement. Other poetry and prose by Doty has addressed the aftermath of 9/11 and the lives of humans and animals. Fire to Fire: New and Selected Poems won the National Book Award for…

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Free

Piano Bar

September 17 @ 10:00 pm
|Recurring Event (See all)
Weekly on the same day until September 18, 2016
Porchbar Gifford House Inn Lobby,
9 Carver St
Provincetown, MA 02657 United States
+ Google Map

Billy Hough on piano and vocals No Cover

Find out more »
$125

Eat.Drink.Art.: A Feast for the Senses

September 24 @ 6:30 pm - 8:30 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map
art

Join Rosewind Gallery and Sage for the Eat.Drink.Art.: A Feast for the Senses dinner series showcasing the art of farm-to-table food surrounded by some of Cape Cod’s finest works. Each event will feature a carefully curated collection of art with an opportunity to meet the artist(s) paired with a seasonal 5-course wine-paired menu.  On September 24th, we are thrilled to be featuring artist Robert Ryan. All events begin at 6:30 pm with champagne and browsing followed by dinner at 7 pm. $125 per…

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Free

Mates Leather Weekend – Prime The Pump

September 29 @ 8:00 pm - 10:00 pm
Bayside Betsy’s,
177 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

For those in town early, come on by Bayside Betsy’s as we “Prime The Pump” before the weekend begins. Hors d’oeuvres provided by Rick of Mates Leather Weekend.

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Free

Mates Leather Weekend – Boot Camp

September 29 @ 10:00 pm - 1:00 am

Shine up your boots and start your MLW “basic training” at this new event.

Find out more »
Free

Mates Leather Weekend – Waterfront Cocktails

September 30 @ 12:30 pm - 3:00 pm
Harbor Lounge,
359 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Enjoy a drink overlooking beautiful Provincetown Harbor at the newest addition to the MLW schedule.

Find out more »
$10

Mates Leather Weekend – Welcome Reception

September 30 @ 4:00 pm - 8:30 pm
Club Purgatory – Gifford House,
9
Carver st at Bradford St., United States
+ Google Map

Start your Friday night right at this meet and greet event and pick up or purchase your Event Pass. Free buffet from 6:00 PM – 8:00 PM. Vegetarian and gluten-free items available. Sponsored in part by the Watership Inn.

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11th Kate Clinton Classic Women’s Flag Football Tournament

September 30 @ 8:00 pm - October 2 @ 5:00 pm

11th annual Kate Clinton Classic  Women’s Flag Football Tournament September 30 - October 2, 2016 Motta Field - Ptown - Parties Each Night Guaranteed 4 Games! Teams, Fans and Loose Women (Individual Players)  Invited! Contact: [email protected] Web: IWFFA.COM  

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Free

Mates Leather Weekend – Dessert and Coffee

September 30 @ 8:00 pm - 9:00 pm
Full Kit Gear,
192 COMMERCIAL STREET
Provincetown, MA, 02657 Select a Country:
+ Google Map

Following the Opening Reception, come eat some sweets and check out the latest in leather & fetish gear.

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$10

Mates Leather Weekend – Uniforms and Cigars

September 30 @ 9:30 pm - 1:00 am
Crown & Anchor,
247 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Military, firefighter, police… What’s your fantasy? Fire up your stogie under the stars or under the tent at this new sub-event for the cigar fetishist.

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Free

Mates Leather Weekend – Free Health Screening

September 30 @ 10:00 pm - 2:00 am
Strength & Clarity Pilates Studio,
170 Commercial St.
Provincetown, MA, MA 02657 United States
+ Google Map

Provincetown’s premier space for men’s sexual health, has partnered with Health Innovations to offer free screenings for gonorrhea, chlamydia, syphilis, hepatitis C and HIV. It’s healthy to be screened every 3-6 months. Get a free 3 oz. bottle of silicone or water base lube when you screen. Questions? Call/text the program nurse at 774-200-7327.

Find out more »
October 2016
$5

Mates Leather Weekend – Leather Market

October 1 @ 11:00 am - 3:00 pm
Boatslip Resort,
161 Commercial Street
Provincetown, MA 02657 United States
+ Google Map

Shop for the finest in leather & Fetish goods, or sell and trade your own gear.

Find out more »
Free

Mates Leather Weekend – Free Health Screening

October 1 @ 3:00 pm - 2:00 am
Strength & Clarity Pilates Studio,
170 Commercial St.
Provincetown, MA, MA 02657 United States
+ Google Map

Provincetown’s premier space for men’s sexual health, has partnered with Health Innovations to offer free screenings for gonorrhea, chlamydia, syphilis, hepatitis C and HIV. It’s healthy to be screened every 3-6 months. Get a free 3 oz. bottle of silicone or water base lube when you screen. Questions? Call/text the program nurse at 774-200-7327.

Find out more »

Ptown Dance Trophy ballroom dance showcase with The Mood Swings Orchestra

October 1 @ 5:00 pm - 9:00 pm
Town Hall,
260 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Boston Open Dancesport The 2016 Provincetown Dance Trophy is a show and ballroom dance competition, outlining the grace and skills of the ballroom dance contestants. Same-sex, reverse role and mainstream couples are welcome to enter the competition. The contests are accompanied with intervals of games and raffles for the audience, professional dance performances of social ballroom dancing. The featuring are disciplines like Bolero, Mambo and Swing as well as the traditional Waltz, Tango, Foxtrot, Cha-cha, Rumba and more. Contests are…

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$5

Mates Leather Weekend – Leather Tea and Meet the Meat

October 1 @ 6:00 pm - 9:00 pm

Not your mother’s tea…but your opportunity to meet the hot men vying for First Mate 2016. What will it take to get your vote?

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$10

Mates Leather Weekend – First Mate Contest

October 1 @ 9:30 pm - 1:00 am
Crown & Anchor,
247 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Register at the Opening Reception or Leather Market for the contest and you could take home a $500.00 cash prize, a $100 gift certificate to Full Kit Gear and the title First Mate 2016. NO REGISTRANTS ACCEPTED after 2:30 PM.

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$10

Mates Leather Weekend – Cookout and Tattoo Contest

October 2 @ 11:30 am - 2:00 pm
Crown & Anchor,
247 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

Join us for hot dogs, hamburgers and salads (vegetarian and gluten-free items available), AND, show us your ink! Last year’s tattoo contest was a hit…now let’s see yours!

Find out more »
Free

Mates Leather Weekend – Free Health Screening

October 2 @ 4:00 pm - 9:00 pm
Strength & Clarity Pilates Studio,
170 Commercial St.
Provincetown, MA, MA 02657 United States
+ Google Map

Provincetown’s premier space for men’s sexual health, has partnered with Health Innovations to offer free screenings for gonorrhea, chlamydia, syphilis, hepatitis C and HIV. It’s healthy to be screened every 3-6 months. Get a free 3 oz. bottle of silicone or water base lube when you screen. Questions? Call/text the program nurse at 774-200-7327.

Find out more »
$10

Mates Leather Weekend – Fetish Party: BOOTS

October 2 @ 4:00 pm - 8:00 pm
Crown & Anchor,
247 Commercial St.
Provincetown, MA 02657 United States
+ Google Map

The BEST party of the year in Ptown…pull off your pants at this sticky, steamy annual favorite. As always, jockstraps encouraged and pants check available.

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$10

Mates Leather Weekend – Rubber Ball and Closing Party

October 2 @ 10:00 pm - 1:00 am
Club Purgatory – Gifford House,
9
Carver st at Bradford St., United States
+ Google Map

Shine up your rubber and roll, bounce or slide up to Purgatory for this final MLW Event.

Find out more »
$125

Eat.Drink.Art.: A Feast for the Senses

October 8 @ 6:30 pm - 8:30 pm
Sage Inn & Lounge,
336 Commercial St.
Provincetown, MA 02657 United States
+ Google Map
rebecca

Join Rosewind Gallery and Sage for the Eat.Drink.Art.: A Feast for the Senses dinner series showcasing the art of farm-to-table food surrounded by some of Cape Cod’s finest works. Each event will feature a carefully curated collection of art with an opportunity to meet the artist(s) paired with a seasonal 5-course wine-paired menu. On October 8th, we are thrilled to be featuring artist Rebecca Bruyn. All events begin at 6:30 pm with champagne and browsing followed by dinner at 7…

Find out more »
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