Oxford Downs Poker Room pairs Vegas style poker with a breezy tiki bar and legit pickleball courts, so you can trade chips for paddles when…
17996 US-301 (Summerfield)
“Oxford Downs Poker Room pairs Vegas style poker with a breezy tiki bar and legit pickleball courts, so you can trade chips for paddles when the flop runs cold. Expect 26 outdoor TVs and Thursday karaoke with DJ Big Country, a reliable local hang.”
Keep it local this week with Flying Boat Tap Room, pouring 28 Florida beers alongside homemade, wood-fired pizza and unique bites that…
9672 SE 58th Ave (Ocala) · ✓ checked Jul 29
“Keep it local this week with Flying Boat Tap Room, pouring 28 Florida beers alongside homemade, wood-fired pizza and unique bites that outkick basic bar food. It’s a relaxed hang where you can taste your way across the state, then refuel with a blistered crust that actually tastes like someone cared.”
When the Florida heat begs for something easy, The Legacy Pool Bar & Grill delivers classic American comfort by the water, from shareable…
17155 Buena Vista Blvd (The Villages) · ✓ checked Jul 28
“When the Florida heat begs for something easy, The Legacy Pool Bar & Grill delivers classic American comfort by the water, from shareable apps and burgers to wings and fresh salads, plus live music Tuesday through Saturday and Monday trivia that makes weeknights way more fun.”
From the The Villages newsletter, October 11, 2026
Craving a little island mood without leaving downtown? The Tipsy Skipper is a boutique 1950s tiki-themed lounge pouring rotating, seasonal…
48 S Magnolia Ave (Ocala)
“Craving a little island mood without leaving downtown? The Tipsy Skipper is a boutique 1950s tiki-themed lounge pouring rotating, seasonal handcrafted cocktails mixed with fresh juices. It’s tucked next to the Marion Theatre, which makes it a perfect pre-show or post-show spot to unwind.”
“Charlie Horse is the kind of easygoing bar and grill that always works for a weeknight: classic pub grub, a full bar, and happy hours that make that second round feel justified. Swing by for karaoke or live music, stay for the laughs and that just-one-more vibe.”
Just up the road in Summerfield, Dragon Flower Winery pours handcrafted wines with tastings that swing from Muscat and Carlos to hibiscus…
11025 SE Hwy 42 (Summerfield) · ✓ checked Sep 10
“Just up the road in Summerfield, Dragon Flower Winery pours handcrafted wines with tastings that swing from Muscat and Carlos to hibiscus (yes, really) and a bourbon barrel aged red blend. Easy spot for a laid back afternoon with friends, and a nice change from your usual grocery-aisle standby.”
From the The Villages newsletter, September 20, 2026
District Bar and Kitchen keeps things easygoing with handcrafted cocktails, elevated pub classics, and plenty of screens for the big game,…
110 SW Broadway St (Ocala)
“District Bar and Kitchen keeps things easygoing with handcrafted cocktails, elevated pub classics, and plenty of screens for the big game, plus live music when you want it louder. Bonus points for those downtown Ocala views and a menu featuring Fort McCoy Beef... not your average bar bite.”
For a legit taste of NOLA without leaving Ocala, Harry's Seafood Bar & Grille brings Cajun and Creole comfort, from jambalaya and the…
24 SE 1st Ave (Ocala)
“For a legit taste of NOLA without leaving Ocala, Harry's Seafood Bar & Grille brings Cajun and Creole comfort, from jambalaya and the Chicken Jolie Blonde to a full bar with their own cocktail creations. Save room for Butter Pecan Cheesecake because, well, priorities.”
Whether you’re chasing crisp craft beer or a night with guitars and good noise, Mutiny Bar Ocala brings live music to a laid-back, piratey…
46 S Magnolia Ave (Ocala)
“Whether you’re chasing crisp craft beer or a night with guitars and good noise, Mutiny Bar Ocala brings live music to a laid-back, piratey hangout that doesn’t take itself too seriously. Go for the brews, stay for the sea-charm and the crowd that somehow turns strangers into shipmates.”
Legacy Bar & Grill is the spot for classic American comfort done right, from shareable apps to juicy burgers, with live entertainment…
6706-000-005, 17155 Buena Vista Blvd (The Villages) · ✓ checked Sep 10
“Legacy Bar & Grill is the spot for classic American comfort done right, from shareable apps to juicy burgers, with live entertainment Tuesday through Saturday and trivia on Mondays. It’s relaxed, neighborly, and, yes, actually by the pool... a solid go-to close to home.”
From the The Villages newsletter, September 15, 2026
Barons Creek Vineyards Tasting Room Ocala pours award-winning wines from California, Texas, Washington, and Spain in a cozy…
16 SW Broadway St (Ocala)
“Barons Creek Vineyards Tasting Room Ocala pours award-winning wines from California, Texas, Washington, and Spain in a cozy historic-district spot with real hometown vibes.”
Black Sheep On Broadway is serving infamous wings, loaded nachos, and seriously good burgers alongside a full bar and live weekend tunes.…
128 SW Broadway St (Ocala) · ✓ checked Aug 7
“Black Sheep On Broadway is serving infamous wings, loaded nachos, and seriously good burgers alongside a full bar and live weekend tunes. Woman-owned and community-minded, it’s the spot for Ocala folks who want comfort food that actually comforts and a vibe that sticks.”
Bank Street Patio Bar keeps downtown nights easy with fresh, locally sourced takes on burgers, sandwiches, and steak, plus a wine and…
120 E Fort King St (Ocala)
“Bank Street Patio Bar keeps downtown nights easy with fresh, locally sourced takes on burgers, sandwiches, and steak, plus a wine and cocktail list built for lingering. It’s the kind of spot where family, food, and fun actually line up… especially when Ocala weather cooperates.”
