* CENTRAL FLORIDA

October 2026
Fish Friday @ Glenview Country Club (The Villages)

October 16 @ 11:00 am - 8:00 pm VITTLES & LIBATIONS

Glenview County Club (The Villages) 3194 Glenview Rd, The Villages, FL, United States

BOGO 1/2 OFF. Friday. The Villages.
HAPPY HOUR @ Chop House (The Villages – Lake Sumter Landing)

October 16 @ 2:00 pm - 4:00 pm Where’s the Happy Hour, Florida?

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Martini Matinee. Weekdays. The Villages - Lake Sumter.
LIVE MUSIC @ Hurricane Dockside Grill (Tavares)

October 16 @ 5:00 pm - 9:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Hurricane Dockside Grill (Tavares) 3351 W Burleigh Blvd, Tavares, FL, United States

Live Music. Fridays-Saturdays Tavares.
Winter Garden Farmers Market

October 17 @ 8:00 am - 1:00 pm Local Florida Markets

Winter Garden Downtown Pavilion and Farmers Market 104 S Lakeview Ave, Winter Garden, Florida

Farmers Market. Saturdays 8am-1pm
Winter Haven Farmers Market

October 17 @ 9:00 am - 1:00 pm Local Florida Markets

Winter Haven Farmers Market @ Grove Roots Brewing Company (Winter Haven) 302 3rd St SW, Winter Haven, Florida

Saturdays
Howl-O-Ween & Downtown Doxie Dash @ Barron Park (LaBelle)

Featured October 17 @ 9:30 am - 4:00 pm Florida for the Holidays

Barron Park (LaBelle) DeSoto Ave, LaBelle, FL, United States

Third Saturday in October
BRUNCH @ Chop House (The Villages – Sumter Landing)

October 17 @ 10:00 am - 3:00 pm VITTLES & LIBATIONS

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Brunch. Saturday-Sunday. The Villages - Lake Sumter.
Brunch @ Bluefin Grill & Bar (The Villages, Brownwood)

October 17 @ 10:00 am - 3:00 pm VITTLES & LIBATIONS

Bluefin Grill & Bar (The Villages, Brownwood) 2738 Brownwood Blvd, The Villages, FL, United States

Brunch. Saturday-Sunday. The Villages - Brownwood
Brunch @ Coastal Del Mar (The Villages, Spanish Springs)

October 17 @ 10:00 am - 3:00 pm VITTLES & LIBATIONS

Coastal Del Mar (The Villages, Spanish Springs) 990 Del Mar Drive, The Villages, FL, United States

Saturdays & Sundays (11am - 3pm)
Bushnell Fall Festival

October 17 @ 10:00 am - 11:00 pm FLORIDA FESTIVALS

Bushnell 215 E McCollum, Bushnell, FL, United States

third Saturday in October
Brunch @ Harvest Restaurant & Bar (The Villages – Brownwood)

October 17 @ 11:00 am - 3:00 pm VITTLES & LIBATIONS

Harvest Restaurant & Bar (The Villages, Brownwood) 3676 Meggison Rd, The Villages, FL, United States

Brunch. Saturday-Sunday. The Villages - Brownwood.
LIVE MUSIC @ Hurricane Dockside Grill (Tavares)

October 17 @ 12:00 pm - 3:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Hurricane Dockside Grill (Tavares) 3351 W Burleigh Blvd, Tavares, FL, United States

Live Music. Saturdays. Tavares.
LIVE MUSIC @ Hurricane Dockside Grill (Tavares)

October 17 @ 5:00 pm - 9:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Hurricane Dockside Grill (Tavares) 3351 W Burleigh Blvd, Tavares, FL, United States

Live Music. Fridays-Saturdays Tavares.
Sunday Brunch & Bottomless Mimosas @ Glenview Country Club (The Villages)

October 18 @ 9:00 am - 1:00 pm VITTLES & LIBATIONS

Glenview County Club (The Villages) 3194 Glenview Rd, The Villages, FL, United States

Brunch & Bottomless Mimosas. Sunday. The Villages.
Brunch @ Bluefin Grill & Bar (The Villages, Brownwood)

October 18 @ 10:00 am - 3:00 pm VITTLES & LIBATIONS

Bluefin Grill & Bar (The Villages, Brownwood) 2738 Brownwood Blvd, The Villages, FL, United States

Brunch. Saturday-Sunday. The Villages - Brownwood
Brunch @ Coastal Del Mar (The Villages, Spanish Springs)

October 18 @ 10:00 am - 3:00 pm VITTLES & LIBATIONS

Coastal Del Mar (The Villages, Spanish Springs) 990 Del Mar Drive, The Villages, FL, United States

Saturdays & Sundays (11am - 3pm)
Brunch @ Harvest Restaurant & Bar (The Villages – Brownwood)

October 18 @ 11:00 am - 3:00 pm VITTLES & LIBATIONS

Harvest Restaurant & Bar (The Villages, Brownwood) 3676 Meggison Rd, The Villages, FL, United States

Brunch. Saturday-Sunday. The Villages - Brownwood.
Karaoke @ Orange Blossom CC (The Villages)

October 18 @ 12:00 pm - 3:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Orange Blossom Hills Country Club (The Villages) 1542 Water Tower Cir, Lady Lake, FL, United States

Karaoke. Sunday. The Villages
LIVE MUSIC @ Hurricane Dockside Grill (Tavares)

October 18 @ 1:00 pm - 4:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Hurricane Dockside Grill (Tavares) 3351 W Burleigh Blvd, Tavares, FL, United States

Live Music. Sundays. Tavares.
Baby Back Rib Night @ Glenview Country Club (The Villages)

October 18 @ 2:30 pm - 8:00 pm VITTLES & LIBATIONS

Glenview County Club (The Villages) 3194 Glenview Rd, The Villages, FL, United States

BOGO. Sunday. The Villages.
HAPPY HOUR @ Chop House (The Villages – Lake Sumter Landing)

October 19 @ 2:00 pm - 4:00 pm Where’s the Happy Hour, Florida?

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Martini Matinee. Weekdays. The Villages - Lake Sumter.
Bottomless Steak Night @ Glenview Country Club (The Villages)

October 19 @ 2:30 pm - 8:00 pm VITTLES & LIBATIONS

Glenview County Club (The Villages) 3194 Glenview Rd, The Villages, FL, United States

Steak Buffet. Monday. The Villages.
BINGO @ 4th Street Bar & Grill (Lake Mary)

October 19 @ 7:00 pm - 9:00 pm B I N G O and Bingo was his name-o

4th Street Bar & Grill (Lake Mary) 132 N 4th St #1200, Lake Mary, FL, United States

Mondays (7-9pm)
HAPPY HOUR @ Chop House (The Villages – Lake Sumter Landing)

October 20 @ 2:00 pm - 4:00 pm Where’s the Happy Hour, Florida?

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Martini Matinee. Weekdays. The Villages - Lake Sumter.
Trivia @ 4th Street Bar & Grill (Lake Mary)

October 20 @ 7:00 pm - 9:00 pm It’s TRIVIA TIME Florida!

4th Street Bar & Grill (Lake Mary) 132 N 4th St #1200, Lake Mary, FL, United States

Tuesdays (7-9pm)
Burger Night @ Glenview Country Club (The Villages)

October 21 @ 11:00 am - 8:00 pm VITTLES & LIBATIONS

Glenview County Club (The Villages) 3194 Glenview Rd, The Villages, FL, United States

BOGO 1/2 OFF. Wednesday. The Villages.
HAPPY HOUR @ Chop House (The Villages – Lake Sumter Landing)

October 21 @ 2:00 pm - 4:00 pm Where’s the Happy Hour, Florida?

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Martini Matinee. Weekdays. The Villages - Lake Sumter.
Trivia @ Belle Glade Country Club (The Villages)

October 21 @ 4:00 pm - 6:00 pm It’s TRIVIA TIME Florida!

Belle Glade Country Club Restaurant (The Villages) 446 Moyer Loop, The Villages, FL, United States

Trivia. Wednesday. The Villages.
Trivia @ Orange Blossom Country Club (The Villages)

October 21 @ 5:00 pm - 7:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Orange Blossom Hills Country Club (The Villages) 1542 Water Tower Cir, Lady Lake, FL, United States

Trivia. Wednesday. The Villages.
Lake County Farmers Market @ Lake County Fairgrounds (Eustis)

October 22 @ 8:00 am - 1:00 pm Local Florida Markets

Lake County Fair Grounds (Eustis) 2101 N. County Road 452, Eustis, FL, United States

Farmers Market. Thursday. Eustis. 8 a.m. - 1 p.m. (October through May)
HAPPY HOUR @ Chop House (The Villages – Lake Sumter Landing)

October 22 @ 2:00 pm - 4:00 pm Where’s the Happy Hour, Florida?

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Martini Matinee. Weekdays. The Villages - Lake Sumter.
Fish Friday @ Glenview Country Club (The Villages)

October 23 @ 11:00 am - 8:00 pm VITTLES & LIBATIONS

Glenview County Club (The Villages) 3194 Glenview Rd, The Villages, FL, United States

BOGO 1/2 OFF. Friday. The Villages.
HAPPY HOUR @ Chop House (The Villages – Lake Sumter Landing)

October 23 @ 2:00 pm - 4:00 pm Where’s the Happy Hour, Florida?

Chop House (The Villages - Lake Sumter Landing) 1045 Old Camp Rd, The Villages, FL, United States

Martini Matinee. Weekdays. The Villages - Lake Sumter.
LIVE MUSIC @ Hurricane Dockside Grill (Tavares)

October 23 @ 5:00 pm - 9:00 pm Listen to some LOCAL LIVE MUSIC, Florida

Hurricane Dockside Grill (Tavares) 3351 W Burleigh Blvd, Tavares, FL, United States

Live Music. Fridays-Saturdays Tavares.
Winter Garden Farmers Market

October 24 @ 8:00 am - 1:00 pm Local Florida Markets

Winter Garden Downtown Pavilion and Farmers Market 104 S Lakeview Ave, Winter Garden, Florida

Farmers Market. Saturdays 8am-1pm
Winter Haven Farmers Market

October 24 @ 9:00 am - 1:00 pm Local Florida Markets

Winter Haven Farmers Market @ Grove Roots Brewing Company (Winter Haven) 302 3rd St SW, Winter Haven, Florida

Saturdays

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October 2026