Spooky Season Just Pulled Up: Your 2026 Tampa Bay Halloween Guide

October in Tampa Bay hits different. The humidity finally eases up, the porches in West Park Village start sprouting pumpkins, and every bar and restaurant within driving distance decides it's time to go full ghoul.

The Tampa Bay Times rounded up the area's best Halloween food and drink events, and we picked our favorites. Whether you want a grown-up night out or something the whole family can do, here's where to spend your spooky season.

Who says trick-or-treating is just for kids? Two Tampa wine bars are pairing five wines with five Halloween candies. Yes, Twizzlers made the cut.

• Chateau Cellars, Tampa: The Hallo-Wine Saturday Stop-In runs from noon to 6 p.m. on Oct. 31. It's casual and self-guided, and matches wines from France, Italy and Spain with treats like M&M's and Starburst. About $42.
• Ybor City Society Wine Bar: Guided wine and candy tastings at 7 p.m. on Oct. 27, 28 or 29. About $42. Book ahead.

If you've been to Miracle or Sippin' Santa at Christmastime, you know this team doesn't do anything halfway. Now they're launching their first-ever Halloween concept, The Haunting, inside Strandhill Public in Tampa Heights.

It runs from Oct. 1 to Nov. 1, and the pub takes reservations. Order the Scream-sicle or the Liquid Lobotomy. Spirit-free drinks and collectible glassware are on the menu too.

Dunedin is a quick drive up from Westchase, and this October its downtown is packed with Halloween fun.

• Spooky Social Club at Sonder Social Club: A seasonal takeover with themed bites like Harvest Apple Mini Bons and cocktails like the Scary Carrie. DJs on weekends, costumes encouraged, through Nov. 1.
• Fenway Fright Night at the Fenway Hotel: Light bites, cocktails, haunted hallway tours, a costume contest and a DJ from 7 to 10 p.m. on Oct. 31. Packages start at $59.
• Soggy Bottom Brewing Co.: Show up in costume on Oct. 31 from 7 p.m. to close for $1 off house pints, plus a costume contest with gift card prizes.

On Oct. 10, Ritual Grounds Cafe and St. Petersburg Distillery are hosting Spooky Island Market, a "spooky swamp hoedown" with more than 100 local vendors from 4 to 10 p.m.

Expect food trucks, ghost tours, a pumpkin patch, live music and a kids zone. General admission is free. Follow @ritualgroundscafe on Instagram for VIP details.

Dust off the bedsheet. These spots are handing out bragging rights.

• Haggaween at Haggard Coffee & Oddities, Brooksville: A family-friendly motorcycle trunk-or-treat with a $100 cash costume prize, from 4 to 7 p.m. on Oct. 17.
• Downtown Crawlers: Haunted bar hops on Halloween Eve and Halloween night in downtown Tampa, Ybor City, South Tampa, downtown St. Pete and New Port Richey. Early bird tickets start around $15 for a group of four.
• Spirits After Dark at The Urban Stillhouse, St. Pete: An adults-only party with tarot and palm readings, cigar rolling and a costume contest, starting at 7 p.m. on Oct. 30. General admission is $99.

The best part of living in Westchase is being close to everything, and this October that means a lot of treats. Pick a spot, grab your crew and we'll see you out there.

One quick tip: dates and prices can change, so check with each venue before you go.

Source: Meaghan Habuda, "Tampa Bay bars and restaurants are getting spooky with Halloween events," Tampa Bay Times, Sept. 24, 2026.

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I'm Bryan Coward, your local Westchase real estate expert. Whether you're relocating to Tampa Bay or looking for your next home in the 33626 area, I'm here to help you make the right move.

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The Bryan Coward Team · Keller Williams Realty · Tampa Bay, FL · Each KW office independently owned and operated. Bryan Coward PA, Florida Licensed Real Estate Broker Associate. Market data reflects general trends and should not be construed as a formal appraisal or guaranteed valuation.