Best events in
Oldsmar

With a culture built around community gatherings and waterfront parks, there are many events and things to do in Oldsmar, FL. Annual festivals like Oldsmar Days & Nights and Oktoberfest bring the city together in R.E. Olds Park. For more low-key outings, local spots offer live music and the massive Oldsmar Flea Market provides a popular weekend destination.

Downtown Oldsmar serves as the main hub for community life, with waterfront concerts at R.E. Olds Park and casual nights out at local restaurants.
The city’s park system is central to its social rhythm, hosting major annual celebrations that draw residents and visitors to the Tampa Bay waterfront.
For a different pace, Mobbly Bayou Wilderness Preserve offers outdoor adventures like hiking and zip-lining, while one of the South's largest flea markets draws weekend crowds.

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Popular in Oldsmar

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Pokémon Club

Tomorrow • 3:30 PM

Oldsmar Public Library

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The Becoming Workshop

Saturday • 9:00 AM

Holiday Inn Express & Suites Tampa Northwest-Oldsmar by IHG

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20th Annual Fall Festival | TICKETS SOLD AT GATE!

Saturday • 11:00 AM + 5 more

8005 Racetrack Rd

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Harvest Moon Happy Hour- Art Exhibition Open House

Thu, Oct 22 • 5:00 PM

3420 Channelside Ct

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Composting Workshop for City of Oldsmar Residents

Sat, Oct 24 • 9:00 AM

Bicentennial Park

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Badass Beer Fest '26

Sat, Nov 7 • 1:00 PM

101 State St E

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BIG TINGZ Comedy Show

Sat, Nov 14 • 9:00 PM + 1 more

Wha Gwaan Jamaica Jamaica

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Pokémon Club

Tomorrow • 3:30 PM

Oldsmar Public Library

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The Becoming Workshop

Saturday • 9:00 AM

Holiday Inn Express & Suites Tampa Northwest-Oldsmar by IHG

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20th Annual Fall Festival | TICKETS SOLD AT GATE!

Saturday • 11:00 AM + 5 more

8005 Racetrack Rd

Check ticket price on event

Harvest Moon Happy Hour- Art Exhibition Open House

Thu, Oct 22 • 5:00 PM

3420 Channelside Ct

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Composting Workshop for City of Oldsmar Residents

Sat, Oct 24 • 9:00 AM

Bicentennial Park

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Badass Beer Fest '26

Sat, Nov 7 • 1:00 PM

101 State St E

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BIG TINGZ Comedy Show

Sat, Nov 14 • 9:00 PM + 1 more

Wha Gwaan Jamaica Jamaica

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Online Events

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How To Be Kind To Yourself - Shahroo Izadi

Tomorrow • 7:00 PM GMT+1

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

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Icons of Conquest: Bayeux Tapestry and Domesday Book

Friday • 2:00 PM GMT+1

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Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Saturday • 9:00 AM EDT

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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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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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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How To Be Kind To Yourself - Shahroo Izadi

Tomorrow • 7:00 PM GMT+1

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thursday • 8:00 AM EDT

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Icons of Conquest: Bayeux Tapestry and Domesday Book

Friday • 2:00 PM GMT+1

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Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Saturday • 9:00 AM EDT

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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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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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Sat, May 15 • 11:00 AM

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8th Annual Tampa Bay Business Expo. FREE 3PM-7PM. 2000+ ATTENDEES

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Hotel Flor Tampa Downtown, Tapestry Collection by Hilton

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Saturday • 8:00 PM

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Mon, Oct 26 • 7:30 PM

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FIREFALL, ATLANTA RHYTHM SECTION, DEREK STONER

Sat, Nov 7 • 2:30 PM

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Tue, Nov 10 • 6:00 PM

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FREE Selwyn Birchwood In Concert

Sun, Dec 6 • 5:30 PM

Safety Harbor Art And Music Center

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PlanetTyrus Tour February 1st, 2027 St Petersburg,FL

Mon, Feb 1 • 7:30 PM

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Sat, May 15 • 11:00 AM

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Free events

General Knowledge Trivia at Beef 'O' Brady's - Oldsmar - $100 in prizes!

Today • 7:00 PM + 52 more

Beef 'O' Brady's - Oldsmar

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Pokémon Club

Tomorrow • 3:30 PM

Oldsmar Public Library

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Survey Says (Family Feud Style Game) @ Hennessey's Bar & Grille (Oldsmar)

Friday • 7:00 PM + 51 more

Hennessy's Bar & Grille

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20th Annual Fall Festival | TICKETS SOLD AT GATE!

Saturday • 11:00 AM + 5 more

8005 Racetrack Rd

Check ticket price on event

Harvest Moon Happy Hour- Art Exhibition Open House

Thu, Oct 22 • 5:00 PM

3420 Channelside Ct

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Composting Workshop for City of Oldsmar Residents

Sat, Oct 24 • 9:00 AM

Bicentennial Park

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O.W.N. Oldsmar Writers Network

Sat, Jun 12 • 10:00 AM

Oldsmar Public Library

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General Knowledge Trivia at Beef 'O' Brady's - Oldsmar - $100 in prizes!

Today • 7:00 PM + 52 more

Beef 'O' Brady's - Oldsmar

Check ticket price on event

Pokémon Club

Tomorrow • 3:30 PM

Oldsmar Public Library

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Survey Says (Family Feud Style Game) @ Hennessey's Bar & Grille (Oldsmar)

Friday • 7:00 PM + 51 more

Hennessy's Bar & Grille

Check ticket price on event

20th Annual Fall Festival | TICKETS SOLD AT GATE!

Saturday • 11:00 AM + 5 more

8005 Racetrack Rd

Check ticket price on event

Harvest Moon Happy Hour- Art Exhibition Open House

Thu, Oct 22 • 5:00 PM

3420 Channelside Ct

Check ticket price on event

Composting Workshop for City of Oldsmar Residents

Sat, Oct 24 • 9:00 AM

Bicentennial Park

Check ticket price on event

O.W.N. Oldsmar Writers Network

Sat, Jun 12 • 10:00 AM

Oldsmar Public Library

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Points of Interest near Oldsmar

Upper Tampa Bay Park

Frequently asked questions about Oldsmar

What are some family-friendly things to do in Oldsmar?

R.E. Olds Park is a great destination for families. It hosts major community events like the annual Celebrate Oldsmar festival, features an amphitheater for concerts, and has plenty of open space for recreation near the waterfront.

Are there many outdoor events and activities in Oldsmar?

Yes, Oldsmar's extensive park system is ideal for outdoor events and fun. Mobbly Bayou Wilderness Preserve offers hiking, canoeing, and zip lines, while R.E. Olds Park is the go-to venue for waterfront festivals and concerts.

Where can I find live music events in Oldsmar?

Several local restaurants and bars host live music events. Spots like Whiskey Wings and the waterfront Jack Willie's Bar, Grill & Tiki are popular choices for catching performances in a relaxed, neighborhood setting.

What is the nightlife scene like in Oldsmar?

Oldsmar has a quiet and relaxed nightlife scene. The focus is on local bars and restaurants that often feature live music. For a wider range of late-night entertainment, many people head to nearby Tampa or Clearwater.

How can I find free events in Oldsmar?

Community parks are the best place to find free events. R.E. Olds Park hosts many public gatherings and festivals with free admission. The Oldsmar Public Library also offers a range of free community programs.

What's the main area for community events in Oldsmar?

Downtown Oldsmar is the center for most community events. R.E. Olds Park, located right on the waterfront in this area, hosts the city's major annual festivals like Oldsmar Days & Nights and Oktoberfest.

Any unique ideas for a date night in Oldsmar?

A dinner with live music is a popular date night option. A waterfront spot like Jack Willie's offers a scenic setting. For something more adventurous, Empower Adventures at Mobbly Bayou has zip lines and an aerial park.

What kind of shopping is popular in Oldsmar?

Market shopping is a big part of the local culture. The Oldsmar Flea Market is one of the largest in the South and a major destination. The city also hosts the weekly Oldsmar Saturday Market.