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    Spooky Bear Weekend in Provincetown!

    October 10, 2023

    Here is your Guide to Halloween in Provincetown.

    Spooky Bear Weekend in Provincetown is an opportunity to “do” Halloween right—Beary Tunes style! Northeast Ursamen will be Spooky!

    Northeast Ursamen Meet & Greet
    Friday Oct 27
    6pm – 8pm

    Come and meet all the Bears at the kick off of Spooky Bear Weekend at Provincetown’s Crown & Anchor in The Dive Bar!!!

    Beary Tunes Heroes and Villains Party
    Friday Oct 27
    9pm – 1am

    Are you bad or good? The Crown & Anchor and Northeast Ursamen present HEROES & VILLAINS, Friday, October 27th at 9pm in The Paramount Club with DJ Corey Craig. With 2 rooms of dancing, 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 Marketplace at The Boatslip
    Saturday Oct 28
    10am – 3pm

    The Bear Marketplace at The Boatslip 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 28

    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:

    Spooky Bear Bingo for a Cause!
    Saturday Oct 28
    2pm – 4pm

    The Crown & Anchor and Northeast Ursamen present SPOOKY BEAR BINGO FOR A CAUSE! Join hosts Morgana Deluxe and Liza Lott for the best bingo game in town! Bring your dabber and try your luck at this event that will benefit SKIP (Soup Kitchen in Provincetown). Come play some bingo for some fabulous prizes!

    The Beary Tunes C0stume Ball and Costume Contest
    Saturday Oct 28
    9pm – 1am

    The OFFICIAL Party of Spooky Bear, The Beary Tunes Costume Ball is your chance to TURN YOUR LOOKS, and get FREAKY with DJ Chris Racine! Featuring 2 Rooms of ‘Barely A-LIVE’ dancing, Ghoulish Go-Go’s, plus 1st, 2nd and 3rd place prizes for best costumes… you never know what Tricks (or Treats) you’ll find at The Crown & Anchor, Saturday, October 28th at 9pm.

    Spooky Bear Drag Brunch
    Sunday Oct 29
    11am & 1pm

    OUR QUEENS HAVE RISEN!!!! Join us for this super special and SAY BOO! Sunday Drag Brunch for Spooky Bear at Crown & Anchor with featuring Delta Miles and friends as they say GAY as many times as possible and watch them sing their faces off while you stuff your faces full. Two shows at 11am and 1pm.

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

    Art House with Provincetown Town Hall
    260 Commercial Street

    Mark Cortale Proudly Presents BIANCA DEL RIO’s return to Ptown for one night only on Sat, Oct. 28th, 2023 for SPOOKY BEAR WEEKEND at Town Hall.

    Crown & Anchor
    247 Commercial Street

    Tim Murray brings his spooky comedy hour ‘Witches!’ to the Crown and Anchor for his Provincetown debut! Hot off his sold-out and award winning run at the Edinburgh Fringe Festival Murray will be playing P-town for two nights only. The show is a mix of drag, stand up and original comedy songs about his favorite pop culture WITCHES!
    The Crown & Anchor’s “funny ghoul” herself, Dina Martina will descend upon the Paramount stage Halloween weekend with her hilarious show, DINA MARTINA HALLOWEENA! As the clock strikes 7:00pm on October 27th, that portly star of the pumpkin patch, Dina Martina, will come back to life and haunt you with songs that’ll thrill, video that’ll chill, and 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!
    The Crown & Anchor is proud to present newest Helltown’s Burlesque show featuring Spookey and a rotating cast of Provincetown’s best performers. We invite you on a Vaudeville journey with a sexy, modern twist. With singing to dancing, drag and even circus acrobatics, this Burlesque Revue serves all genders, all bodies, and anyone looking for just the right amount of tease.
    What happens when 3 of Provincetown’s drag divas have a seance to talk to their favorite dead icons? You get an hour of performance possession, spooks, and haunts…DEAD DIVA! Join Delta Miles, Roxy Pops and Qya Cristal for this special Halloween edition of DIVA! as they invoke the spirits of their favorite musical artists from the afterlife and beyond! This show is sure to get you in the spirit(s) and take you on a “time warp!” Don’t miss this killer, “Thriller” show bound to make you “wanna dance with somebody”. Let’s just hope that somebody is alive ????!
    IT’S ALIVE! Just when you thought she was dead and gone, Provincetown’s award-winning Crown & Anchor drag brunch Queen is back from the grave and she’s bringing her ghoulish pals with her! Join Mackenzie along with Qya Cristal, Scarlett Strauss, Mahoganny and Austin Tyler for a very special, spooky ZOMBIE DRAG BRUNCH!
    This undead brunch features delicious nosh by award winning chef Kelly Fields, and will be unlike anything you’ve experienced in this life, or the next! Zombie looks highly encouraged! Prizes for the best zombie fashions! Get those tickets before they’re gone…like our BRAAAAIIINNNNSS!
    Back for its second year, Austin Tyler’s ARE YOU AFRAID OF THE DORK invites you to the funniest campfire story gathering you’ve ever experienced. Join Austin as he shares his completely true collection of stories, infusing them with his cheeky charm and wit at Crown & Anchor in Provincetown.
    A dark immersive Cabaret experience in Provincetown’s Crown & Anchor. Written & directed by Brittany Rolfs and Joao Santos, The Green Fairy will transport you to “The Lounge”, where you’ll be immersed in the world of Summer (Rolfs) and Solomon (Santos), a traveling jazz duo, accompanied by The Pianist (Andrew Sheranian) in what might be a final, possibly fatal, performance.
    But why? What’s the secret they’re holding? Why are they acting so strange? Who dies?….Well, It’s Halloween, babe.

    Gifford House
    9 Carver Street

    Get ready for the spookiest showdown in Provincetown as FAG BASH takes on BEARS IN SPACE Spooky Bear Weekend at the Gifford House!!! Join us for this hair raising spooktacular!!! FAG BASH vs BEARS IN SPACE for this intergalactic showdown!!!
    Step into a world of mystery and enchantment at Gifford House “House of Spirits” Halloween Masquerade Ball!

    Governor Bradford
    312 Commercial Street

    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!
    The stage is set: Curtains up!, light the lights!
    It’s a Dragalicious Karaoke night!

    Pilgrim House
    336 Commercial Street

    Through her signature story and song, Madame Grave Intentions will conjure up memories of Halloween past and warble her way through rancid renditions of terrifying tunes. It seems that a summer spent in the hell-fire Palm Springs sun has baked her brain; her hypochondria is in full bloom, and she’s convinced she won’t survive the performance. You’ll die laughing… unless Madame dies first.
    LUXX LIAISON & QYA CRYSTAL BITCHCRAFT at Provincetown’s Pilgrim House. Are you a good witch… or a bad bitch? A magic spellbook releases a sexy coven of witches to tempt a young boy between light and dark magic.

    Post Office Cafe & Cabaret
    303 Commercial Street

    “A Spooky Encore Performance”! Todd Buonopane: : “Single and… Loving It?” returns as our Spooky Bear feature at Provincetown’s Post Office Cabaret for one night only!
    Happy Spooky Bear Weekend! Come one come all! Friday October 27th at Provincetown’s Post Office Cabaret, kick off Halloween season correctly, with Boylesque: The Meat Market! Come, see the most talented, naughty, hysterical, and downright spooky male entertainers around. This show is gonna be so scary, they’re gonna scare their own pants right off!
    The Anita Cocktail Variety Hour is thrilled to be their THIRD SEASON. Hostess and Emcee Anita Cocktail and drag cast members Abby Cummings and Raquel Blake as they welcome guest entertainers from all over the country, performing everything from Spot-On celebrity impersonations, hysterical comedy, Pop Divas, Burlesque and Live Singing.  A great way to celebrate a Birthday, anniversary or even a divorce, a night with Anita and the girls is the way to go!
    The Post Office Cafe is THRILLED to welcome Anita Cocktail’s Drag Brunch back to host her SOLD-OUT! Have fun with Anita, Abby, Raquel, Lakia and all of the incredible entertainers bring to PTown. This season’s promises familiar favorites like Leslie Avery, Zola Powell, Ivy League and Lawanda Jackson as well as some new and exciting queens making their Provincetown premier! 11am and 12:30pm Seatings!

    Provincetown Brewing Co.
    141 Bradford Street

    Kick off Spooky Bear Weekend with your friends at Provincetown Brewing Co. during our 5th Annual FLIP CUP TOURNAMENT! Founded on PBC’s progressive ideals and our driving concept of #Draftivism, we invite you to join us for our 5th Annual, Double-Elimination style Flip Cup Tournament Friday night 10/27/23. Which team will take home the grand prize, trophy, and coveted bragging rights for the year?!?!
    BEER. DANCING. CRUISING. It must be TRUCKSTOP. And this time, PBC is hosting with some classic beats by Andrew Lenox. Hosted by Cain Marko, come spend your Sunday afternoon ‘Bobbing for Weiners’ or, just hang by the Urinals. We GUARANTEE not only a SPOOKY, but a SLEAZY good time! Presented by The Crown & Anchor and The Provincetown Brewing Co, and proudly partnering with The Urban Bear. See ya’ll in the stalls!

    Red Room
    258 Commercial Street

    Tammie Brown’s Halloween Spooktacular with Provincetown’s Red Room Tammie’s Spooky and fun Halloween show!
    The Golden Gays Halloween Show present: RING RING! It’s the Libertine Belle Murder Musical at Provincetown’s Red Room.
    Back for its 3rd year, our famous weekly Underwear Party gets spooky for Halloween at Red Room in Provincetown. Come dance to the happy beats of DJ Tony T.  Clothing check available. Tickets sold at the door only.
    Back for its 4th year, Ptown’s biggest halloween party and costume party is October 28th at Red Room in Provincetown! This years party, POSSESSED III with 2 floors of dancing, drinks and pop up ghouls, and a $1000 cash prize for best costume, will be hosted by our pal and drag superstar TAMMIE BROWN! Sooooo, buy your tickets early as we always sell out! Tickets are tiers started at $15!

    The Club
    193A Commercial Street

    Qya Cristal & The Bart Weisman Trio with Matt Hutchinson on piano, Ron Ormsby on bass, and Bart Weisman on drums. $20 Food/Beverage Minimum per person required.

    The Provincetown Theater
    238 Bradford Street

    Just in time for Halloween, the Provincetown Theater is bringing back its frighteningly good leading man from their revered 2019 mounting of Sweeney Todd, the Tony Award-nominated Broadway star Tom Hewitt in the regional premiere of Aaron Mark’s critically acclaimed one-man thriller, Another Medea.

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

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