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Best events in
St. Leo

Events and things to do in St Leo, FL, blend historic small-town charm with modern suburban energy. The area is defined by the contrast between Dade City's quaint, historic downtown and the bustling, family-focused complexes in Wesley Chapel. This creates a diverse scene with everything from classic car shows on brick-lined streets to contemporary live music.

An evening in historic Dade City often flows from a relaxed dinner to intimate live music at a cozy venue like The Twisted Oak.
Wesley Chapel offers concentrated entertainment hubs, with stand-up at Side Splitters Comedy Club or themed music nights at the open-air KRATE at the Grove.
Community traditions are a big part of local life, including the Annual Kumquat Festival in Dade City and the monthly Fresh Market at Wiregrass.

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Events near St. Leo

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The Soul Violin Experience: Live in Tampa primary image

The Soul Violin Experience: Live in Tampa

Tomorrow • 8:00 PM

New Tampa Performing Arts Center

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ASEMFL 2026 Annual Meeting

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Marshall Student Center

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Brews & Baby Moos

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Hooves and Boots Farm

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Cigar & Bourbon Fundraiser Benefiting Friends of Joshua House! primary image

Cigar & Bourbon Fundraiser Benefiting Friends of Joshua House!

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Stonewater Grill

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Saddlebrook Resort- Cars on the Fairway primary image

Saddlebrook Resort- Cars on the Fairway

Sat, Nov 21 • 10:00 AM

Saddlebrook Resort

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The Royal Treatment with the Frozen Sisters primary image

The Royal Treatment with the Frozen Sisters

Sun, Dec 13 • 2:00 PM

Party N Style-Kids Spa, Haircuts, and Parties

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The COME CLOSER Tour | Tampa, FL primary image

The COME CLOSER Tour | Tampa, FL

Thu, Jan 7 • 7:00 PM

Grace Family Church - Lutz

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COAH Women's Retreat 2027 primary image

COAH Women's Retreat 2027

Fri, Feb 19 • 3:00 PM

Lakewood Retreat

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The Soul Violin Experience: Live in Tampa primary image

The Soul Violin Experience: Live in Tampa

Tomorrow • 8:00 PM

New Tampa Performing Arts Center

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ASEMFL 2026 Annual Meeting primary image

ASEMFL 2026 Annual Meeting

Friday • 8:00 AM

Marshall Student Center

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Brews & Baby Moos primary image

Brews & Baby Moos

Sunday • 10:00 AM

Hooves and Boots Farm

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Cigar & Bourbon Fundraiser Benefiting Friends of Joshua House! primary image

Cigar & Bourbon Fundraiser Benefiting Friends of Joshua House!

Fri, Nov 13 • 6:00 PM

Stonewater Grill

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Saddlebrook Resort- Cars on the Fairway primary image

Saddlebrook Resort- Cars on the Fairway

Sat, Nov 21 • 10:00 AM

Saddlebrook Resort

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The Royal Treatment with the Frozen Sisters primary image

The Royal Treatment with the Frozen Sisters

Sun, Dec 13 • 2:00 PM

Party N Style-Kids Spa, Haircuts, and Parties

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The COME CLOSER Tour | Tampa, FL primary image

The COME CLOSER Tour | Tampa, FL

Thu, Jan 7 • 7:00 PM

Grace Family Church - Lutz

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COAH Women's Retreat 2027 primary image

COAH Women's Retreat 2027

Fri, Feb 19 • 3:00 PM

Lakewood Retreat

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Nearby cities

Tampa

29 miles away

St. Petersburg

46 miles away

Lakeland

28 miles away

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Safety Harbor

36 miles away

Carrollwood

24 miles away

Pinellas Park

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Wesley Chapel

10 miles away

Winter Haven

39 miles away

Riverview

35 miles away

Four Corners

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Westchase

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East Lake-Orient Park

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Clermont

35 miles away

Lecanto

36 miles away

Temple Terrace

22 miles away

Town 'n' Country

30 miles away

Citrus Park

27 miles away

The Villages

43 miles away

Leesburg

41 miles away

Gulfport

49 miles away

Mount Dora

49 miles away

Land O' Lakes

15 miles away

Coleman

34 miles away

Tampa

29 miles away

St. Petersburg

46 miles away

Lakeland

28 miles away

Clearwater

40 miles away

Brandon

28 miles away

Orlando

49 miles away

Largo

43 miles away

Lake Magdalene

21 miles away

Dunedin

38 miles away

Winter Garden

44 miles away

Safety Harbor

36 miles away

Carrollwood

24 miles away

Pinellas Park

43 miles away

Wesley Chapel

10 miles away

Winter Haven

39 miles away

Riverview

35 miles away

Four Corners

39 miles away

Westchase

29 miles away

East Lake-Orient Park

24 miles away

Clermont

35 miles away

Lecanto

36 miles away

Temple Terrace

22 miles away

Town 'n' Country

30 miles away

Citrus Park

27 miles away

The Villages

43 miles away

Leesburg

41 miles away

Gulfport

49 miles away

Mount Dora

49 miles away

Land O' Lakes

15 miles away

Coleman

34 miles away

Online Events

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Gunpowder Plot - punishing the plotters

Today • 7:30 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Tomorrow • 1:00 PM GMT

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The World of Bunny vs Monkey Workshop with Jamie Smart primary image

The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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Physicians Financial Wellness Conference 2026 primary image

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Gunpowder Plot - punishing the plotters primary image

Gunpowder Plot - punishing the plotters

Today • 7:30 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence primary image

No Title, No Permission, No Problem: Harnessing the Power of Influence

Tomorrow • 1:00 PM GMT

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The World of Bunny vs Monkey Workshop with Jamie Smart primary image

The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

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Lean Global Connection 2026 primary image

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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The Walrus Talks at Home: Canada After America primary image

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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Physicians Financial Wellness Conference 2026 primary image

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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Corn as a partner and gift giver: Voices of respect primary image

Corn as a partner and gift giver: Voices of respect

Wed, Nov 18 • 10:00 AM CST

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Washington Crossing the Delaware / The Crossing - Film History Livestream primary image

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about St. Leo

Where can I find live music events near St. Leo?

Head to historic Dade City for intimate shows at The Twisted Oak, which features rock, blues, and folk artists. For a modern outdoor setting, KRATE at the Grove in Wesley Chapel hosts regular themed music nights, including its monthly Country Night and Latin Night.

What's the comedy scene like in Wesley Chapel?

The primary venue for comedy is Side Splitters Comedy Club in Wesley Chapel. The intimate showroom hosts nationally known headliners as well as showcases for local talent, making it a popular destination for a night of laughs and drinks.

Are there good spots for a date night?

Wesley Chapel's Grove complex offers multiple date night activities in one place. Couples can enjoy a comedy show, play mini-golf, try axe-throwing, or see a movie before grabbing a bite to eat at one of the many restaurants in the area.

What are some family-friendly things to do?

The Joy-Lan Drive-In Theatre in Dade City is a nostalgic local favorite for families. For active families, the Wiregrass Ranch Sports Campus in Wesley Chapel hosts youth sporting events, and the nearby Pioneer Florida Museum & Village holds community festivals.

How do events in Dade City compare to Wesley Chapel?

Dade City events reflect its historic character, with gatherings like the monthly Dade City Cruise-In. In contrast, Wesley Chapel's event scene is more contemporary and centered around large entertainment complexes like KRATE at the Grove, which hosts a variety of events.

Does the area have any recurring outdoor markets or festivals?

Yes, the region hosts several popular annual and monthly outdoor events. The Fresh Market at Wiregrass in Wesley Chapel happens twice a month year-round, while downtown Dade City is home to the large Annual Kumquat Festival and the annual Rattlesnake Festival.

What kind of food and drink events are typical?

The area's food events often center on community festivals and markets. The Annual Kumquat Festival in Dade City celebrates the local citrus with themed foods, and the Fresh Market at Wiregrass in Wesley Chapel features local food vendors.

Can you find free community events?

Yes, many community events are free to attend, such as the Dade City Cruise-In classic car show. The monthly themed nights at KRATE at the Grove also offer free admission to enjoy the atmosphere and live music, with food and drinks available for purchase.