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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Spin and Soul with AJ Hall

Saturday • 8:00 PM

Babe Coffee Lounge

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Pumpkin Halloween Paint Splash

Sunday • 9:00 AM

Branchton Park

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K-POP CIRCUS SHOW LIVE! – WESLEY CHAPEL, FL

Fri, Oct 16 • 6:00 PM

Center for the Arts at Wesley Chapel

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Fearless Women's Summit- Tampa 2026

Sat, Oct 17 • 8:00 AM

Sierra Conference Center

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The Soul Violin Experience: Live in Tampa

Thu, Nov 5 • 8:00 PM

New Tampa Performing Arts Center

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ASEMFL 2026 Annual Meeting

Fri, Nov 6 • 8:00 AM

Marshall Student Center

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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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COAH Women's Retreat 2027

Fri, Feb 19 • 3:00 PM

Lakewood Retreat

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Spin and Soul with AJ Hall

Saturday • 8:00 PM

Babe Coffee Lounge

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Pumpkin Halloween Paint Splash

Sunday • 9:00 AM

Branchton Park

Check ticket price on event

K-POP CIRCUS SHOW LIVE! – WESLEY CHAPEL, FL

Fri, Oct 16 • 6:00 PM

Center for the Arts at Wesley Chapel

Check ticket price on event

Fearless Women's Summit- Tampa 2026

Sat, Oct 17 • 8:00 AM

Sierra Conference Center

Check ticket price on event

The Soul Violin Experience: Live in Tampa

Thu, Nov 5 • 8:00 PM

New Tampa Performing Arts Center

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ASEMFL 2026 Annual Meeting

Fri, Nov 6 • 8:00 AM

Marshall Student Center

Check ticket price on event

The Royal Treatment with the Frozen Sisters

Sun, Dec 13 • 2:00 PM

Party N Style-Kids Spa, Haircuts, and Parties

Check ticket price on event

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

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Clearwater

40 miles away

Brandon

28 miles away

Largo

42 miles away

Orlando

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Lake Magdalene

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Safety Harbor

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Wesley Chapel

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Dunedin

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Winter Garden

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Winter Haven

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Riverview

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Four Corners

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Clermont

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East Lake-Orient Park

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Citrus Park

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Temple Terrace

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Palm River-Clair Mel

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The Villages

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Coleman

34 miles away

Lealman

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Tampa

29 miles away

St. Petersburg

46 miles away

Lakeland

28 miles away

Clearwater

40 miles away

Brandon

28 miles away

Largo

42 miles away

Orlando

49 miles away

Lake Magdalene

22 miles away

Safety Harbor

36 miles away

Wesley Chapel

10 miles away

Dunedin

38 miles away

Pinellas Park

43 miles away

Winter Garden

44 miles away

Carrollwood

25 miles away

Winter Haven

39 miles away

Riverview

34 miles away

Four Corners

39 miles away

Clermont

35 miles away

Westchase

29 miles away

East Lake-Orient Park

24 miles away

Citrus Park

27 miles away

Land O' Lakes

15 miles away

Town 'n' Country

29 miles away

Temple Terrace

22 miles away

Ocoee

48 miles away

Leesburg

41 miles away

Palm River-Clair Mel

29 miles away

The Villages

43 miles away

Coleman

34 miles away

Lealman

45 miles away

Online Events

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Humanitarian Water Engineering Fall 2026

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

Thu, Nov 5 • 1:00 PM GMT

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Virtual - Powerful Gottman Method Couples Therapy Tools

Fri, Nov 20 • 8:00 AM CST

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The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

Check ticket price on event

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

Humanitarian Water Engineering Fall 2026

Check ticket price on event

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

Thu, Nov 5 • 1:00 PM GMT

Check ticket price on event

Virtual - Powerful Gottman Method Couples Therapy Tools

Fri, Nov 20 • 8:00 AM CST

Check ticket price on event

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

Check ticket price on event

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.

Events near St. Leo

Spin and Soul with AJ Hall

Pumpkin Halloween Paint Splash

K-POP CIRCUS SHOW LIVE! – WESLEY CHAPEL, FL

Fearless Women's Summit- Tampa 2026

The Soul Violin Experience: Live in Tampa

ASEMFL 2026 Annual Meeting

The Royal Treatment with the Frozen Sisters

COAH Women's Retreat 2027

Spin and Soul with AJ Hall

Pumpkin Halloween Paint Splash

K-POP CIRCUS SHOW LIVE! – WESLEY CHAPEL, FL

Fearless Women's Summit- Tampa 2026

The Soul Violin Experience: Live in Tampa

ASEMFL 2026 Annual Meeting

The Royal Treatment with the Frozen Sisters

COAH Women's Retreat 2027

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Nearby cities

Tampa

St. Petersburg

Lakeland

Clearwater

Brandon

Largo

Orlando

Lake Magdalene

Safety Harbor

Wesley Chapel

Dunedin

Pinellas Park

Winter Garden

Carrollwood

Winter Haven

Riverview

Four Corners

Clermont

Westchase

East Lake-Orient Park

Citrus Park

Land O' Lakes

Town 'n' Country

Temple Terrace

Ocoee

Leesburg

Palm River-Clair Mel

The Villages

Coleman

Lealman

Tampa

St. Petersburg

Lakeland

Clearwater

Brandon

Largo

Orlando

Lake Magdalene

Safety Harbor

Wesley Chapel

Dunedin

Pinellas Park

Winter Garden

Carrollwood

Winter Haven

Riverview

Four Corners

Clermont

Westchase