Spooky Bear Halloween 2022 Guide to Must Do Events!

October 2, 2022

Here is your Guide to Halloween in Provincetown.

Spooky Bear Weekend is an opportunity to “do” Halloween right—Bear style but for everyone! Northeast Ursamen will be Grimm’s Beary Tales with a weekend of revelry, costumes, and some treats!

Northeast Ursamen Meet & Greet
Friday Oct 28
6pm – 8pm

Meet and Greet in the Dive Bar at the Crown & Anchor. Come meet some of the members of the Northeast Ursamen at Spooky Bear! Drinks and appetizers will be available!

Grimm’s Beary Tales: Heroes and Villains Party
Friday Oct 28
9pm – 1am

Grimm’s Beary Tales: Heroes and Villains Party – Are you good or bad? Show us your best looks for Spooky Bear at The Paramount Club with DJ Chris Racine. With 2 rooms of dancing, live performances, and ghoulish go-go’s we look forward to seeing your best look with $500 cash for best costume! Get your tickets now and avoid the line!

Bear Mart at Spooky Bear 2022
Saturday Oct 29
10am – 3pm

The Bear Mart boasts 12-15 vendors each year including photography, ceramics, sculptures, t-shirts, and a make your own harness station! Spooky Bear T-Shirts will also be on sale by the Northeast Ursamen! The Boatslip Resort and Beach Club will be open so you can enjoy a cocktail while you shop! Come see all that it has to offer this year! Each of our vendors has committed to making a donation to the Provincetown Soup Kitchen.

4pm – The World Famous Tea Dance at the Boatslip Resort and Beach Club.
Don’t miss out ALL WEEKEND the Spooky Bear Tea Dance!

Dune Tour with Art’s Dune Tours
Saturday Oct 29
1pm

Dune Tour with Art’s Dune Tours: Enjoy the beauty of the dunes in Ptown with experienced tour guides! $33 per person. Call Art’s Dune Tours to book: 508-487-1950 and for more information, check out their website: https://www.artsdunetours.com/

Bingo for a Cause!
Saturday Oct 29
4pm – 6pm

Bingo for a Cause! Located in the Paramount Room at the Crown & Anchor. Northeast Ursamen will be raising money for Q Plus, our beneficiary for the Spooky Weekend so come play some bingo for some fabulous prizes! $25 online or at the door, and buys your first card! $2 for each additional bingo card! Every dollar counts!

Grimm’s Beary Tales: Costume Ball and Costume Contest
Saturday Oct 29
9pm – 1am

Grimm’s Beary Tales: Costume Ball and Costume Contest in the Paramount Room at the Crown & Anchor! Sign up for the contest as you enter the Paramount! Cash prize of $1000 to the winner! Which Beary Tales character will win the grand prize at Spooky Bear Weekend?

Spooky Bear Drag Brunch
Sunday Oct 30
11am & 1pm

Spooky Bear Drag Brunch

Spooky Bear Drag Brunch with 2 shows at 11am and 1pm in the Paramount Room at the Crown & Anchor. $25 online or at the door with a $25 additional food minimum.

There is a never ending schedule of fun events. ptownie wants to make sure you know about all our favorites!

Crown & Anchor
247 Commercial Street
508-487-1430

The Crown & Anchor’s “funny ghoul” herself, Dina Martina will descend upon the Paramount stage Halloween weekend with a hilarious new show, DINA MARTINA HALLOWEENA! As the clock strikes 7:30pm on October 28th & 29th, that portly star of the pumpkin patch Dina Martina will come back to life and haunt you with new songs that’ll thrill, new video that’ll chill, and new costumes that’ll scare the bejesus out of you! Whether you’re a ghost, a ghoul or a zombie, you won’t want to miss the frighteningly funny DINA MARTINA HALLOWEENA!

Thirsty Burlington is BACK with a spooky twist on her hit show from this summer! Thirsty takes you down memory lane… all the way back to 1975 in her brand new show based on the iconic Cher Show! Join her LIVE as she sings all the hit songs you remember while wearing the fabulous costumes Cher was famous for!

Provincetown’s first ALL local, queer, body-positive burlesque experience is back and sexier and spookier than ever! Bringing the body, gore, camp and spice, Mack’niFREAK will flirt, dazzle and dance with your deepest, darkest desires. Mackenzie and her demons are sure to make you blush in this daring and devilish fantasy.

A terrifically terrifying event to jazz up this Halloween! Ptown’s own LIZA LOTT brings back her 2019 Halloween HIT to the Crown & Anchor for 1 performance only! Known for her spot-on Liza Minnelli imprecation, Miss Lott always delivers with her hilarious comedy and ALL LIVE VOCALS! Featuring tons of spooky surprises and special guests from beyond the grave, you don’t want to miss out!

“Are You Afraid Of The Dork?” is an hour-long, campfire style, scary story experience – a frightening & funny recounting of REALghost encounters! Along with terrifying tales, Austin will be debuting live, for the very first time, comedy from a wildly funny jokester whose time came too soon. Care for a scare…? Celebrate Halloween weekend right and grab your tickets now for this two-night only event!

Art House with Provincetown Town Hall
260 Commercial Street
800-838-3006

JINKX MONSOON Provincetown — RuPaul’s Drag Race Winner and Current Star of ALL STARS returns to Provincetown for two shows at Jinkz Monsoon with Major Scales at the piano for Spooky Bear Weekend at Town Hall! Jinkx Monsoon is one of the brightest stars on the drag circuit.

Red Room
258 Commercial Street
508-487-4870

House of La Rue and Red Room present POSSESSED – A Halloween dance party and costume contest.
2 floors of dancing, drinks, and pop up performances! Costume contest withn a grand prize of $1,000 CASH.

The Ptown Famous Underwear party is on Halloween Weekend at the Red Room. Boys and (sometimes girls) dance the night away to the happy beats of DJ Tony T. Friday the 28th of October at 10pm. Tickets available at the venue the night of party. Varied cover. 21 plus. Complimentary clothing check.

NYC comedian Sam Morrison (The Drew Barrymore Show) grapples with the death of his partner. He makes grief hilarious through tales of love, diabetes and seagull attacks. Sugar Daddy is fresh off its hit run at Edinburgh Festival, where it was one of the best reviewed comedies of the festival, was featured in The Times, BBC Scotland, and received 5 star reviews from POW! Showbiz, Broadway Baby, Broadway World.

Drain your misery with a special one night Halloween comedy show ALL WALLOWS SIEVE with Anne and Saltine. Dance Party & Costume Contest to follow with DJ Alex Dropo!

Pilgrim House
336 Commercial Street
508-487-6424

She’s freaky, and she’s kooky and altogether spooky!
It’s Tammie Brown’s Halloween Spectacular at Pilgrim House, Spooky Bear Weekend.

Halleluiah! Provincetown’s Longest Running Drag Brunch continues at Pilgrim House every Sunday.
Get your Mimosa on early! The Landing Bar Opens at 10 AM on Sunday!
Indulge in BRUNCH, BOOZE & BLASPHEMY with our rotating cast of Sinful, Sassy Soul Sisters at the House of Pilgrim!

Post Office Cafe & Cabaret
303 Commercial Street
508-487-0087

BEARLESQUE: A Very Spooky Burlesque is coming to Post Office for one night only, October 28th! Come see some of the most sexy, hysterical, and downright spooky male-burlesque performers around. This show is sure to titillate, and also we can promise that this show will scare the pants right off of the Bearlesque boys! Don’t miss this! Happy Halloweekend!

Todd Buonopane (30 Rock, Unbreakable Kimmy Schmidt) and Michael Buchanan (Book of Mormon, The Addams Family) have been friends for nearly 20 years. And they’ve been gay even longer than that! But how did they get soooooo gay? Todd & Michael will explore that question with the songs of Broadway, 80’s pop and even the Muppets!

The Anita Cocktail Variety Hour Provincetown — The Anita Cocktail Variety Hour, Ptown’s HOTTEST Drag Revue is thrilled to be returning to the PO Cabaret after a knock-out first season. With entertainers from PTown and Beyond, the Anita Cocktail Variety Hour is a hour of the finest drag from all over New England and beyond.

Schartt$ Creek! A Jamie Morris Parody Ptown — SCHARTT$ CREEK is an unauthorized parody of the record-setting, Emmy Award-winning sitcom. From the twisted mind of “Schartt$ Creek” picks up where the series left off as we join the Rose family who converges on Ptown to support David who has been abandoned on his honeymoon!

Hop on over to the Post Office Cafe and catch the Anita Cocktail’s Drag Brunch! Theres no better way to wake up then with a little cocktail in your cup. Every week Anita is joined by some of her closest friends to bring you some of the best entertainment from New England and Beyond.

The Club
193A Commercial Street
508-487-1527

LEA DeLARIA headlines with The Mike Flanagan Quartet at THE CLUB PROVINCETOWN. Space is limited, so get your tickets now! Saturday, October 29 @ 8pm & Sunday, October 30 @ 11:00 AM

Governor Bradford
312 Commercial Street
508-487-2781

Everyone’s favorite rock band, SPACE PUSSY!
One Show Only of the biggest parties of the season and featuring 25 local and celebrity guests! There’s only ONE real Halloween Night at The Governor Bradford! Tix at The Bradford starting October 15.

Your stop for a full schedule of Provincetown events, programs, shows, parties, and more!: Provincetown Event Calendar

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Spooky Bear Halloween 2022 Guide to Must Do Events!

Here is your Guide to Halloween in Provincetown.

Spooky Bear Weekend is an opportunity to “do” Halloween right—Bear style but for everyone! Northeast Ursamen will be Grimm’s Beary Tales with a weekend of revelry, costumes, and some treats!

Northeast Ursamen Meet & Greet Friday Oct 28 6pm – 8pm

Grimm’s Beary Tales: Heroes and Villains Party Friday Oct 28 9pm – 1am

Bear Mart at Spooky Bear 2022 Saturday Oct 29 10am – 3pm

Dune Tour with Art’s Dune Tours Saturday Oct 29 1pm

Bingo for a Cause! Saturday Oct 29 4pm – 6pm

Grimm’s Beary Tales: Costume Ball and Costume Contest Saturday Oct 29 9pm – 1am

Spooky Bear Drag Brunch Sunday Oct 30 11am & 1pm