Nightlife in Lakeland Highlands

South Shore Music Festival & Chili Cook-Off at International Showmans Club on November 8 (Up to 48% Off)

South Shore Music Festival & Chili Cook-off

International Showmans Club

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Country stars Gwen Sebastian and Jason Michael Carroll headline outdoor charity festival featuring a chili cook-off and cornhole tournament

$17.25 $9

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Saturday Night Laughs in New Tampa for One, Two, or Four on September 6–December 6 (Up to 46% Off)

Saturday Night Laughs in New Tampa

Heritage Isles Golf & Country Club

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Top-notch local and national comedians, including Tampa favorite Trish Keating, stoke laughter in a lush country club

$11.54 $8

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Bar Food at Hogan's Beach (Up to 52% Off). Two Options Available.

Hogan's Beach

Rocky Point

Watch the big game on flat-screen TVs while filling your plate with wings, burgers, pizza, and more; bar has more than 20 beers on tap

$25 $12

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Dinner Show for One or Two from The Murder Mystery Company (52% Off)

The Murder Mystery Company

The Spaghetti Warehouse

Interactive dinnertime murder mystery that stars professional actors tests diners’ sleuthing skills throughout a multicourse meal

$120 $58

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In-Home Wine Tasting for Four or Eight with Complimentary Bottle of Wine from PRP Wine International (Up to 87% Off)

PRP Wine International

University Square

Wine consultants travel to homes, pouring samples from four or six different bottles for small groups

$150 $19

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One or Two Tickets to Any Speed-Dating Event from Tampa Singles Events (Up to 57% Off)

Tampa Singles Events

On Location

Like-minded singles in their 20s through 40s mingle for five minutes each at venues across Tampa

$35 $17

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Pub Food and Drink at Durty's Bar and Grille (Up to 50% Off)

Durty's Bar and Grille

St. Petersburg

Tear into a burger and stay a while with a game of pool or join in with a nightly event, like karaoke or trivia

$20 $11

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$5 for $10 Groupon — City Billiards Lic

City Billiards

West and East Lealman

Local businesses like this one promote thriving, distinctive communities by offering a rich array of goods and services to locals like you

$10 $5

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Standup-Comedy Show and Drinks for Two with Option for Dinner at Snappers Grill & Comedy Club (Up to 58% Off)

Snappers Grill & Comedy Club

Palm Harbor

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Guests enjoy standup comedy while digging into entrees and sipping premium drinks

$36 $15

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Local Craft-Beer Tasting for Two or Four at The Pint and Brew (Up to 52% Off). Five Options Available.

The Pint and Brew

Palm Harbor

Sample four craft beers from breweries such as Florida Avenue Brewing Co. and Green Bench Brewing Co.; BYO snacks with tailgate option

$28 $14

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Wine and Sangria Tasting with Keepsake Glasses for Two or Four at Tarpon Springs Castle Winery (Up to 53% Off)

Tarpon Springs Castle Winery

Tarpon Springs

Each visitor sips several wines and a full glass of sangria; pairs take home a bottle of wine, a sangria-making kit, and two crystal glasses

$101.50 $49

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Wine-Tasting Package for Two or Four with Tour and Take-Home Bottles at Aspirations Winery (Up to 54% Off)

Aspirations Winery

Clearwater

Enjoy wine samples and food pairings before taking a behind-the-scenes tour, leaving with souvenir glasses and a 750ml bottle of wine

$70 $35

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$29 for General Admission for One to the Pirate's Dinner Adventure Show "Vampirates" ($31 Value)

Pirate's Town

Southwest Orange

Diners feast as Pirates put on a Vampire-themed Halloween thriller aboard an 18th-century Spanish ship set in a 300,000-gallon indoor lagoon

$31 $29

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David Nail, Frankie Ballard or Jerrod Niemann on September 27, November 28, and December 6 (Up to 30% Off)

Jerrod Niemann, David Nail, and Frankie Ballard

House of Blues Orlando

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Three country stars on the rise take the House of Blues stage on the heels of hot new albums

$27 $18.90

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Women of Faith: From Survival to Revival at Amway Center on October 10 and 11 (Up to 30% Off)

Women of Faith: From Survival to Revival

Amway Center

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A Bible-focused weekend of inspiration and entertainment, including music, speakers from churches around the world, and comedy

$99 $69

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Nick Carter & Jordan Knight at Plaza Live on October 21 at 8 p.m. (Up to 37% Off)

Nick Carter & Jordan Knight

Plaza Live

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Members of New Kids on the Block and the Backstreet Boys debut a new collaborative album on a tour full of harmonies and choreography

$55.62 $35

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Improv Comedy Show Including Beer or Wine for Two at Sak Comedy Lab, August 23–December 27 (Up to 50% Off)

Sak Comedy Lab

Central Business District

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Comics compete for laughs, clash in competitions, and create characters, songs, and scenarios on the spot

$40 $20

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Two Hours of Pool with Appetizers and Drinks for Two or Four at Trick Shots (Up to 51% Off)

Trick Shots

Multiple Locations

Groups shoot pool for two hours while munching wings and cheese sticks and sipping drinks

$36.99 $18

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Speed-Dating Event for One or Two from Party4Ten (Up to 54% Off)

Party4Ten

Orlando

Speed-dating events meet at local hot spots, giving singles the chance to meet potential love interests and new friends

$25 $12

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$15 for a Pitcher of Beer and Two Hours of Pool for Four at Backstage Billiards I-Drive ($28 Value)

Backstage Billiards I-Drive

Orlando

Beginners and pool sharks alike can rack up games on any of the 24 Brunswick tables

$28 $15

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$15 for $40 Worth of Cocktails, Beer, and Wine at NV Art Bar

NV Art Bar

Central Business District

Visitors sip blueberry ales, oatmeal-infused stouts, and crisp wines with hints of grapefruit and guava in a lounge and art gallery

$40 $15

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Hookah Package with Refill and Fruit Head for Two or Four at Royal Hookah & Cigar Lounge (Up to 52% Off)

Royal Hookah & Cigar Lounge

Orlando

Hookah packages include everything needed for a relaxing evening including refills and fruit heads, such as apple

$28 $14

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Seafood and Mexican-American Food for Lunch or Dinner at Señor Frog's (Up to 50% Off)

Señor Frog's

Southwest Orange

Tacos, burritos, burgers, and barbecue make mouths water at this festive eatery filled with bright colors and live music

$30 $15

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Breeders Cup at the Ranch for One or Two at Premier Sports Campus on November 1, at 12 p.m. (Up to 50% Off)

Derby Day at the Ranch

Premier Sports Campus

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Watch the Breeders Cup World Championships on a giant LCD screen, with music from local favorites

$150 $99

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"Working" for Two at Annie Russell Theatre on September 26–October 4 (Up to 52% Off)

"Working"

Annie Russell Theatre

25 characters, each with a different job, explore the American Dream as they sing songs by Stephen Schwartz and James Taylor

$42 $20

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$33 for Wine Tasting at The Wine Room on Park Avenue ($53 Value)

The Wine Room on Park Avenue

Winter Park

156 wines from temperature-controlled Enomatic wine-dispensing machines; Groupon purchasers receive 20% off retail wines on return visit

$53 $33

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Select Local Merchants

Bedrock Cafe serves up a menu of mammoth-sized bar eats and cold beer in a lively sports bar environs. Guests can start game night off right with smothered fries ($7.49), heaped with cheddar cheese, smoked bacon, and creamy ranch dressing. Wings ($6.95 for 10) come in a myriad of flavors, such as mild, medium, hot, blackened, cajun garlic crystal, BBQ, pterodactyl, and more. Dig into archaeological good taste with the Bedrock Philly hot sandwich ($7.95), or nosh on a classic 8 oz. flame broiled burger ($5.95) with cole slaw, pickle, and French fries. The catfish fingers seafood platter ($6.95) lets one embrace whiskery underwater creatures without the risks of tickling your cheeks. Although catching a grueling baseball defeat over a meal might deplete morale, troops can rally with a karaoke round of “Don’t Stop Believing” on Wednesday nights, while geometry hotshots can prove their mathematical prowess on the pool table.

3201 US Highway 98 S
Lakeland,
FL
US

The independent Evolution stimulates the Lakeland scene by selling an eclectic selection of both mainstream and underground music while providing an intimate venue for local and touring musicians to present their craft. Evolution's stock consists of T-shirts ($10+), CDs and vinyl records ($1+), and posters for music fans to coat their empty walls with artist admiration. Peruse Evolution's thousands of vinyls, from timeless classics, including The Beatles and AC/DC, to exciting new artists (though Bob Dole's ambient-metal album is currently sold out). Evolution hosts shows nearly every weekend, featuring artists advancing the cause of rock, hip-hop, folk, and more.

119 S Kentucky Ave
Lakeland,
FL
US

It's not exactly 100 bottles of beer on the wall?in fact, it's more than three times that. Sourced from locations scattered across the globe, The Brass Tap boasts more than 40 brews on tap and hundreds upon hundreds of bottled craft beers. The selection ranges from Chimay Cinq Cents Tripel, a Belgian White imported straight from Baileux, to local brews like Cigar City's citrusy Jai Alai IPA. The drinks pair nicely with the down-home decor and toe-tapping lineup of musical acts, as well as the menu of premium cigars, sourced from places like Nicaragua, the Dominican, and Milton Berle's old sport coats.

37916 Pasco Ave
Dade City,
FL
US

In order to enter Brew Hounds Sports Lounge, one has to pass between murals of a football field and basketball court. Inside, flat-screen televisions glow with the day's games, blending with the neon of beer signs. Visitors looking to create some competition of their own will find it at the row of electronic dart boards, upon the pool table, or staring into the Yuengling mirror, waiting for the stranger on the other side to blink.

318 Havendale Blvd
Auburndale,
FL
US

The menu at Tanner’s Pub celebrates bar food from all over the world with a mix of traditional American comfort food and English pub grub. Classic dishes with upscale twists include bacon-wrapped filet mignon and crab penne with asparagus and white-wine sauce.

325 W Central Ave
Winter Haven,
FL
US

With free wine tastings all day Monday through Saturday and beer tastings on Tuesday nights and Saturday afternoons, Tapping The Vine lubricates taste buds with its extensive collection of lesser-known libations and globally imported specialty wines and craft beers. Browse aisles brimming with fermentation favors and malted liquid gold while the friendly staff offers helpful suggestions to determine if customers' palates might prefer the tarty taste of a Wallace Brooks pinot gris ($16) or the bittersweet chocolatey Charles Smith Velvet Devil merlot ($16), among other white, red, and dessert wines. Barley buffs can analyze the feel of various brews, such as the flavorful Rogue Hazelnut Brown Nectar ($6.99) and organic Scarecrow golden pale ale ($4.69). Like the mouths of famous rappers, Tapping The Vine wouldn't be complete without an assortment of accessories, including professional-grade bottle openers ($9) and champagne stoppers ($5).

7110 Cypress Gardens Blvd
Winter Haven,
FL
US