57 happy hours

Happy Hour in Leesburg, FL

The best drink specials, food deals, and happy hour spots in Leesburg. Updated for 2026.

Happy Hours

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All Happy Hours in Leesburg

The Next Bite

4.7 (42)

venezuelan restaurant

10401 US-441 Ste 82, Leesburg, FL 34788

9600 US-441, Leesburg, FL 34788

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Perkins Restaurant & Bakery

4.1 (2,105)

restaurant

27811 US-27, Leesburg, FL 34748

27405 US-27 #109, Leesburg, FL 34748

2229 Citrus Blvd, Leesburg, FL 34748

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Cracker Barrel Old Country Store

4.4 (4,130)

american restaurant

9450 US-441, Leesburg, FL 34788

9616 US-441, Leesburg, FL 34788

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Oakwood Smokehouse & Grill

4.6 (1,914)

barbecue restaurant

27745 US-27, Leesburg, FL 34748

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Caribe Restaurant & Bar

4.8 (130)

restaurant

1107 W N Blvd Ste 26, Leesburg, FL 34748

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The Brick & Barrel Public House

4.3 (992)

restaurant

209 W Main St, Leesburg, FL 34748

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Ski Beach Bar and Grill

4.6 (4,264)

american restaurant

21 Dozier Cir, Leesburg, FL 34748

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Turners Kitchen + Bar

4.4 (778)

new american restaurant

114 S 5th St, Leesburg, FL 34748

32900 Countryside Blvd, Leesburg, FL 34748

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Wolf Branch Brewing Co.

4.8 (101)

restaurant

707 W Main St, Leesburg, FL 34748

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Wolfy’s Leesburg Restaurant

4.3 (2,598)

diner

918 N 14th St, Leesburg, FL 34748

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Prime 3 on Main Steakhouse

4.1 (332)

restaurant

610 W Main St, Leesburg, FL 34748

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Chesapeake Bay Grille at Arlington Ridge

4.5 (212)

american restaurant

4467 Arlington Ridge Blvd, Leesburg, FL 34748

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McCracken’s Irish Pub

4.6 (737)

restaurant

719 W Main St, Leesburg, FL 34748

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Gator Bay Bar and Grill

4.4 (1,088)

american restaurant

10320 County Rd 44, Leesburg, FL 34788

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Bubba's Crab & Seafood

4.6 (471)

seafood market

1301 E Main St, Leesburg, FL 34748

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Cousin Vinnies Family Sports Restaurant

4.4 (1,923)

sports bar

10700 US-441, Leesburg, FL 34788

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Ranchito Mexican Grill

4.3 (940)

mexican restaurant

911 W N Blvd, Leesburg, FL 34748

755 N 14th St, Leesburg, FL 34748

1331 N 14th St, Leesburg, FL 34748

10601 US-441 Ste C12, Leesburg, FL 34788

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Brooklyn's Pizzeria & Italian Restaurant

4.4 (797)

pizza restaurant

27405 US-27, Leesburg, FL 34748

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Genos Pizza and Grinders (Bassville Park)

4.2 (373)

pizza restaurant

11240 Northern Ave Suite#101, Leesburg, FL 34788

1850 US-441, Leesburg, FL 34748

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Two Old Hags Wine Shoppe

4.7 (145)

wine bar

410 W Main St, Leesburg, FL 34748

215 W Main St, Leesburg, FL 34748

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Hamrick Family Vineyards

5 (23)

wine bar

118 S 2nd St, Leesburg, FL 34748

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Vanderbrew Coffee Shop

4.9 (124)

coffee shop

201 W Main St, Leesburg, FL 34748

26736 US-27, Leesburg, FL 34748

1707 South St, Leesburg, FL 34748

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Willy Buck's Backyard Grill

4.4 (46)

barbecue restaurant

1317 S 14th St, Leesburg, FL 34748

10401 US-441, Leesburg, FL 34788

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Rompeolas Cafe

4.9 (105)

puerto rican restaurant

2115 Citrus Blvd J, Leesburg, FL 34748

305 Pine St, Leesburg, FL 34748

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Magnolia's Oyster Bar

4.5 (649)

seafood restaurant

201 W Magnolia St, Leesburg, FL 34748

1200 W Main St, Leesburg, FL 34748

2005 W Main St, Leesburg, FL 34748

1704 Citrus Blvd, Leesburg, FL 34748

10820 County Rd 44, Leesburg, FL 34788

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Mamadukes Brewery & Eatery

5 (5)

fast food restaurant

215 W Main St, Leesburg, FL 34748

1008 W Dixie Ave, Leesburg, FL 34748

9924 US-441, Leesburg, FL 34788

411 W Main St, Leesburg, FL 34748

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Taqueria Santa Lucia Leesburg

4.6 (21)

taco restaurant

2999 W Main St, Leesburg, FL 34748

1403 S 14th St, Leesburg, FL 34748

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Soulful Flavor Food Truck

4.5 (38)

restaurant

1219 W Main St, Leesburg, FL 34748

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Simply Nutrition

4.9 (56)

health food restaurant

703 W Main St, Leesburg, FL 34748

9926 US-441, Leesburg, FL 34788

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Dip-A-Dee-Donuts and More

4.6 (449)

donut shop

1376 W N Blvd, Leesburg, FL 34748

11240 Northern Ave Ste 105, Leesburg, FL 34788

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AMSTERDAM SMOKE SHOP & LOUNGE

4.6 (121)

bar

1323 S 14th St #703, Leesburg, FL 34748

2204 Griffin Rd, Leesburg, FL 34748

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Lemmy’s Gourmet Italian Ice & Sorbet

5 (47)

ice cream shop

117 S 4th St, Leesburg, FL 34748

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Frequently Asked Questions

What are the best happy hours in Leesburg?

DiscoverHappyHours lists 57 bars and restaurants with happy hour specials in Leesburg, FL. Browse all options with drink and food deals.

What time is happy hour in Leesburg?

Most happy hours in Leesburg run between 3 PM and 7 PM on weekdays. Some venues offer daily happy hours and late-night specials. Check individual listings for exact times.

Where can I find cheap drinks in Leesburg?

Browse our Leesburg happy hour guide to find bars with drink specials starting from $3-$5 for beer and $5-$8 for cocktails during happy hour.

Own a bar or restaurant in Leesburg?

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