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Bear Week
Wiener Roast & Pool Party 2026

Provincetown's Bear Week Weiner Roast is an annual tradition held at the Brass Key.

  • Event Dates

    From: Awaiting dates
    To: Awaiting dates

  • Key Highlights

    • Guest DJs
    • Pool Party
    • Live Shows
    • Fittest Bears
    • Hottest Men

Bear Week Wiener Roast & Pool Party 2026

Provincetown's Bear Week Weiner Roast is an annual tradition held at the Brass Key.

  • Stay close to the party and PTown's busy gay bars at the “Fabulous” rated Crowne Pointe Inn, offering guests spacious rooms, highly-rated breakfasts and perfect location.

The Event

  • Awaiting dates- Typically the final Friday night of PTown Bear Week
  • Brass Key Guest House plays host to the Bear Week Wiener Roast & Pool Party this year.
  • Dance by the pool with the fittest bears and otters and enjoy live shows and guest DJs.
  • The Brass Key has always thrown a HUGE party for Carnival, and this is the first time that they are hosting one for Bear Week.
  • Spend the afternoon flirting with hundreds of Bear Week's hottest men while mingling with guest hosts, both in and out of the Brass Key's iconic pool.

The Big Weiner Contest

  • The Winning Wiener will receive a $200 cash prize, a smokeless mini-grill courtesy of Tito's – for your future wiener needs, and all the adoration one could desire from the Big Wiener judge (and, of course, the rest of the party too.)
  • Contest participants must pre-register at check-in and wear special swimwear during the contest.

The Venue

  • The Brass Key Guest House – Surrounding a terraced courtyard, this posh, adult-only guesthouse in 9 historic buildings (some dating to the 1790s) caters to gay men. It is a block from the shops and dining on Commercial Street.
  • Freebies include continental breakfast, evening wine and cheese receptions, and drinks served by a heated infinity pool and hot tub. There's also a spa, a rooftop deck, a cosy cocktail lounge and a DVD lending library.

Recommended Hotels in Provincetown

  • Known for its vibrant atmosphere and rich LGBTQ+ history, PTown offers a range of gay bars, clubs, and events.
  • Popular neighboring areas include Commercial Street, where you'll find a bustling mix of shops, restaurants, and entertainment venues.

The following hotels have high ratings and are close to the gay scene of Commercial Street:

Gabriel’s,    Anchor Inn,    Beaconlight,   Inn at Cook Street.

Gay Map of Provincetown

Provincetown itself has two main drags, Commercial Street and Bradford Street. P'town can be divided into three sections, the quiet and peaceful West End, the bustling downtown center, and the East End, which has a number of galleries and guesthouses.

Address: 7 Cook St, Provincetown, MA 02657

  • Historic East End inn with serene gardens.
  • Tasteful rooms; some with porches or views.
  • Hearty homemade breakfast each morning.
  • Steps to galleries; walkable to the scene.
  • Website

Address: 12 Winthrop Street Provincetown, MA 02657

  • Boutique inn steps from Commercial Street.
  • Calm rooms, comfy beds, strong showers.
  • Courtyard fire pits and porch hangouts.
  • Easy walk to bars, galleries, and harbor.
  • Website

Address: 102 Bradford Street Provincetown, MA 02657

  • Steps from Town Hall; peaceful garden setting.
  • Suites with fireplaces, decks, kitchenettes.
  • Hearty homemade breakfast; pet-friendly.
  • Central stay, quiet once inside the gates.
  • Website

Address: 176 Commercial St Provincetown, MA 02657

  • Waterfront stay with wide Provincetown Bay views.
  • Rooms with decks and gas fireplaces.
  • Light breakfast; sunset porch is the highlight.
  • Steps to Commercial St fun; calm at night.
  • Website

Address: 6 Masonic Place Provincetown, MA 02657

  • P-town’s classic three-room gay club.
  • Pop, throwbacks, and house till late.
  • Courtyard breathers; fast, friendly team.
  • Busy weekends; cover on peak nights.
  • Open: Daily 4pm-1am, Friday Saturday Sunday 12pm-1am
  • Facebook

Address: 186 Commercial St, Provincetown, MA 02657

  • Cave-style lounge just off Commercial Street.
  • Classic cocktails with a coastal twist.
  • Warm late-night mood; mixed friendly crowd.
  • Great pre-club stop or end-of-night sip.
  • Open: Daily 12pm-1am
  • Website

Address: 359 Commercial St, Provincetown, MA 02657

  • Waterfront lounge with sweeping bay views.
  • Soft seating, low light, easy mood.
  • Martinis, spritzes, and steady pours.
  • Sunset hotspot with a friendly team.
  • Open: Thursday 3pm-9pm, Friday 3pm-11pm, Saturday 1pm-11pm,
    Sunday 1pm-9pm
  • Facebook

Address: 161 Commercial St Provincetown, MA 02657

  • Iconic bayfront tea dance with sunset views.
  • Pop and house, big crowd, high energy.
  • Cover charge, wristbands, fast-moving line.
  • Perfect launch pad for a P-town night.
  • Open: 4pm–7pm (in season, daily)
  • Website

Address: 258 Commercial St, Provincetown, MA 02657

  • Modern club at the Gifford House.
  • DJ nights, live shows, drag and guests.
  • Strong sound, quick bars, clear sightlines.
  • Late crowd; cover on busy weekends.
  • No fixed daily hours.
  • Opens for shows and parties.
  • Typical shows run 4–9 pm.
  • Club nights run late. Check the calendar for your date.
  • Website

Address: 247 Commercial St Provincetown, MA 02657

  • Central hotel-venue with bars, stages, and pool.
  • Drag, cabaret, DJs, and live music nightly.
  • Modern rooms; pro staff; smooth operations.
  • Right on Commercial St; walk to everything.
  • Open: Bar/restaurant 11am–1am daily.
  • Wave Bar 4pm–1am daily.
  • Shows: start times vary; many begin 7pm–9pm
  • Pool bar (summer): afternoons to early evening.
  • Website

Address: 11 Carver St, Provincetown, MA 02657, United States

  • Basement late-night club with a cruisy vibe.
  • Pop and house; busiest after 11 pm.
  • Theme nights: underwear, gear, leather.
  • Fast bar, tight room, big weekend energy.
  • Open: Daily 10pm-1am
  • Website

Address: 9 Carver St, Provincetown, MA 02657

  • Front-porch cocktails on Commercial Street.
  • Calm early, lively later; great people-watching.
  • Classics done well, fast friendly service.
  • Perfect warm-up before a night out.
  • Open: Daily 5pm–1am
  • Website

Address: 10 Carver Street Provincetown, MA 02657

  • Intimate lounge at the Brass Key.
  • Low light, fireplace, leather seating.
  • Classic cocktails mixed with care.
  • Courtyard sips near Commercial Street.
  • Open: Daily 5pm-1am
  • Facebook

Address: 207 Commercial Street Provincetown, MA 02657

  • Waterfront deck with wide harbor views.
  • Drinks from the bar, food from mall vendors.
  • Chill vibe, sunset is the main event.
  • Steps from Commercial St—great meet-up spot.
  • Open: Tue–Thu & Sun 11am–7pm Fri–Sat 11am–9pm Closed Monday
  • Website

Address: 177 Commercial St Provincetown, MA 02657

  • Waterfront spot with big bay views.
  • Chowder, lobster rolls, hearty plates.
  • Busy brunch; fast, friendly service.
  • Deck and window tables are the prize.
  • Open: Sun–Thu: 8am–8pm Fri–Sat 8am–12am
  • Breakfast/Brunch 8:00–13:00; Lunch 13:00–16:00
  • Website

Recommended Hotels in Provincetown By Booking

Book with confidence. Get the best Prices from our partner Booking.com
We have chosen hotels in Provincetown that keep you close to all the shops, restaurants & bars

Anchor Inn Beach
4 Star, Luxury

Anchor Inn Beach House
Booking.com
  • 4 Star – Unique Decor, Large Windows and Balconies
  • Close to the gay district
  • Refrigerators, antique-style
  • Provincetown property with uniquely decorated rooms, refrigerators, Wi-Fi, close to Pilgrim Monument and Park.

Beaconlight House
4 Star, Readers Choice

Booking.com
  • 4 Star – Outdoor Hot Tub, Flower Gardens
  • Close to the gay district
  • En suite bathroom, flat-screen TV
  • Features en suite bathrooms, flat-screen TVs with DVD players, refrigerators, outdoor hot tub, and flower gardens.

Inn at Cook Street
4 Star, Great Value

Booking.com
  • 4 Star – In The Heart of Art Gallery District
  • Close to the gay district
  • Unique decorations, flat-screen TV
  • In Provincetown's art gallery district, historic inn with individually decorated rooms, daily hot breakfast.

Hotel at Gabriel's
4 Star, Location

Booking.com
  • 4 Star – Large Courtyard and Gardens
  • Close to the gay district
  • Cable TV, fireplace, balcony
  • In central Provincetown, offers free WiFi, rooms with cable TVs, fireplaces, warm colors, and plush bedding.

Video Brass Key Pool Parties

Highlights from previous pool events at The Brass Key Guest House

Carpe Diem Guesthouse Provincetown

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