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Ocala’s drinking establishments are diverse—and growing! Whether you’re looking for a private speakeasy or a trendy spot for a craft cocktail, Ocala’s bar scene has the pour for you.
Written & Compiled By Cynthia Brown & Dean Blinkhorn
DOWNTOWN
THE TIPSY SKIPPER—The Tipsy Skipper aims to be one of Florida’s best craft cocktail bars. Located downtown next to the Marion Theatre, The Tipsy Skipper is a boutique tiki-themed upscale lounge, featuring rotating and seasonal handcrafted cocktails along with secret menu items hidden throughout the town.
You Must Try: The Pearl Diver, a sort-of Hot Buttered Rum that comes in a signature ribbed glass and features whipped butter, sugar, spices, and three different rums.
48 South Magnolia Avenue 352-282-0377 thetipsyskipperocala.com
The Tipsy Skipper
ANTI-MONOPOLY DRUG STORE SPEAKEASY—Located inside The Lodge and true to past speakeasy history, you must have a password for entry. They offer craft and traditional cocktails and a limited appetizer menu. Follow them on Facebook for history lessons on prohibition and to obtain the password.
You Must Try: The Pink Lady, a classic, ginbased cocktail with grenadine that gives this distinctive drink its namesake color.
36 South Magnolia Avenue 352-289-1390 (The Lodge) anti-monopoly-drug-store.business.site
THE THIRSTY COBBLER—Created by the owners of Ivy on the Square this speakeasy brings history to life. Specialty cocktails, trendy true-to-era atmosphere, password (from Facebook) required for entry.
You Must Try: The Soul-less, a delightful honey/ginger combination.
11 East Fort King Street 352-622-5550 facebook.com/thethirstycobbler
The Thirsty Cobbler
MUTINY OCALA—Inviting all pirates, punks and scallywags, Mutiny is a pirate-themed tavern/gastropub located in the heart of downtown. Punk music, food, and a specialty beer list.
You Must Try: One of the beers on tap, like the Hammer of the Shaolin, an imperial stout with a whopping 10.75% APV.
46 South Magnolia Avenue mutinyocala.com
THE COURTYARD ON BROADWAY—Located on Broadway Street right in the heart of downtown Ocala, The Courtyard offers beer, wine, and a tapas bar. Enjoy the relaxed atmosphere in the outside courtyard, hung with bistro lights and a fire pit. Play video games, giant Jenga, or even giant beer pong!
You Must Try: Something from their generous wine selection. Just ask the server for a suggestion based on your tastes and you might find a new favorite!
120 Southwest Broadway Street 352-354-2029 facebook.com/thecourtyardonbroadway
O’MALLEY’S ALLEY—Ocala’s classic Irish pub on the downtown square. Drink specials every night, daily lunch specials, and live acoustic music inside or on the large outdoor patio.
You Must Try: A pint of Guinness would be quite appropriate.
24 South Magnolia Avenue 352-351-2172 facebook.com/omalleysalley
INFINITE ALE WORKS—An award-winning brewery that specializes in Belgian inspired beers. Check out their website for the most up-to-date draft list containing over 20 assorted flavors. Food, live music, patio, growlers, and a beer club.
You Must Try: One of their own creations like Witfinite, a Belgian-style wheat that’s a two-time “Best Florida Beer” medal winner.
304 South Magnolia Avenue 352-512-0212 infinitealeworks.com
THE KEEP DOWNTOWN—Upstairs, the red-carpet lounge is where patrons eat, relax, enjoy live entertainment, sip wine, and socialize. The menu offers light and delicious items including sandwiches, salads, pizza, and desserts. The retail wine shop offers elegant, custom gift baskets for corporate and personal gift giving. The store also sells premier wines, champagnes, and wine accessories. Downstairs in the rear section is a cozy, Mediterranean-style outdoor patio. Patrons are welcome to enjoy premium cigars and hookahs.
You Must Try: An eight-bottle boutique wine tour held on the third Wednesday of the month in the upstairs lounge, which is accompanied by specialty hors d’oeuvres.
36 Southwest 1st Avenue 352-369-9858 thekeepdowntown.com
THE TERRACE ON THE SQUARE— Enjoy amazing views of historic downtown Ocala from the outdoor terrace located on the second story of the Hilton Garden Inn while being served high-end cocktails, beer, wine, and specialty foods. Entertainment nightly.
You Must Try: A mimosa with their Sunday Brunch overlooking the Downtown Square.
120 East Silver Springs Boulevard 352-581-6060 facebook.com/theterraceonthesquare
THE BLACK SHEEP ON BROAD- WAY—The Black Sheep on Broadway is a cozy take on a traditional gastropub. Located in the heart of Ocala, enjoy music, craft beer, a full liquor bar, and a creative food menu.
You Must Try: This gastropub has many great beers, including several varieties by Sailfish Brewing Company.
128 Southwest Broadway Street 352-622-1207 theblacksheeponbroadwayocala.com
Bank Street Patio Bar
Photo by John Jernigan
BANK STREET PATIO BAR—Located in a former bank building, Bank Street offers locally sourced fresh food, craft beers, and cocktails in an upscale atmosphere with nightly entertainment.
You Must Try: A glass from the awesome wine menu or a specialty craft cocktail like Rita’s A Hottie, a blend of white tequila, mango, jalapeno, and salt.
120 East Fort King Street 352-877-8667 bankstreetpatio.com
THE CORKSCREW—A unique winery and brewery experience where you are the cellar master. Begin the brewing process on site and in as little as 4-8 weeks you are ready to bottle and label your very own custom wine or beer! You can also enjoy a glass of custom wine or craft beer in the new cellar.
You Must Try: This one’s on you. Pick your wine varietal and preference and come back in 4-8 weeks to try your own unique selection.
16 Southwest Broadway 352-402-0158 thecorkscrewwinery.com
EAST OCALA
FLYING BOAT TAPROOM—Two airline pilots that have a passion for the “Golden Era” of flying boats along with the love of craft beer recently opened this unique spot. Combine that with a young, talented chef with a passion for creating the best homemade wood-fired pizza accompanied with unique dishes and a drive for providing the best service possible. This taproom features 28 of the finest beers Florida brewers have to offer, plus the aforementioned wood-fired pizza, and other special cuisine.
You Must Try: They always have 28 of the finest Florida brews on tap. Look for Hey Hefé, a delicious Hefeweizen from Ellipsis Brewing in Orlando.
9672 Southeast 58th Avenue 352-545-2337 flyingboattaproom.com
The Flying Boat Taproom
MILLER’S ALE HOUSE—A local restaurant and sports bar known for generous portions, low prices, warm service, and shareable appetizers served in an atmosphere that includes more than 60 TVs; large, open-air patios; beckoning bars; and spacious booths and tables. There are over 35 beers on tap; a vast selection of signature cocktails; and all-day, everyday drink specials.
You Must Try: An easy hangout with great all-day prices like the 5-for-$19.99 bucket special or the $14.99 margarita pitchers.
305 Southeast 17th Street 352-620-8989 millersalehouse.com/locations/Ocala
MAE BEER & TAPAS—Four brothers with a passion for Latin food and craft beer have come together to create this Ocala gem. Try specialty Margaritas, Sangria, IPAs, and domestics in this cozy spot. A must try? The Mexican Street corn!
You Must Try: An excellent selection of distinctive wines and beers along with an amazing menu of small bites, so order what you like and ask your server for the perfect pairing!
4901 East Silver Springs Boulevard, Suite 503 352-877-8500 maebeerandtapas.com
WEST OCALA
THE CRAZY CUCUMBER—An eatery and bar with a relaxed atmosphere and a warm modern industrial vibe. The perfect place for lunch, drinks with friends, dinner with family or date night. Karaoke every Thursday on the patio and happy hour every day from 2-7pm.
You Must Try: They have lots of great beers and wines, but the specialty drinks are a lot of fun. Try The Bitch Slap, a rumbased drink with a tasty blend of peach, pineapple, and orange juices.
4414 Southwest College Road 352-390-6969 thecrazycucumber.com
The Crazy Cucumber
HIATUS BREWERY—A brewpub that features on-site crafted brews where you can preorder growlers to go also offers
a full-service restaurant with handhelds, wings, flatbreads, and pretzels larger than your head. Check out the screen upon entering for all the most current brews.
You Must Try: Get a four-pack crowler of Time Stands Still, an American bock based on a turn-of-the-century recipe that’s both dark and sweet.
6230 Southwest College Road 352-509-4867 hiatusbrewing.com
JUNIPER GENERAL STORE—At the Juniper General Store, the goal is to offer customers the best products made as locally as possible. While sipping on an espresso-based drink, wine, or craft beer, you can shop their carefully curated provisions and gifts. Having a get-together? Bring in your own appetizers and meals to enjoy at their huge gathering table.
You Must Try: They have an amazing coffee bar, but drink-wise their beer selections on tap are the main attraction. If they have it, look for Aw Jeez by Angry Chair Brewing, a fruited sour of strawberries, raspberries, vanilla, and cinnamon.
6998 US Hwy. 27, Suite 112 352-509-4006 facebook.com/thejunipergeneralstore
Travis Arenburg, partner at Juniper General Store
Photo by John Jernigan
YELLOW PONY PUB—Located at the World Equestrian Center’s hotel and boasting an outdoor patio and fireplace, The Yellow Pony offers shareable starters, pub fare, traditional draft beers, bourbon, and whiskey. A globally inspired pub and garden, The Yellow Pony pairs craft beer and creative cocktails with fresh ingredients. Whether joining for a quick lunch, a cold beer, or dinner with friends, you are sure to have a wonderful time in this vibrant social space.
You Must Try: The Rosemary Lavender Smash, which uses EG Rosemary Lavender Vodka, lime, and lavender syrup. Be sure to ask for an order of the fish ‘n’ chips, too!
8510 Northwest 17th Lane 352-414-7865 yellowponyocala.com
Yellow Pony Pub
Photo: Ethan Tweedie
