Your version of Internet Explorer is no longer supported. Please upgrade your browser.

Arts Events and Things to do in Oakland, MD

Search for something you love or check out popular events in your area.

Mentalist - Richard Passaro
Sat, Jun 20, 7:00 PM
Irwin · 200 Main St
Mentalist - Richard Passaro
Sat, Jun 20, 7:00 PM
Irwin · 200 Main St
Almost full
6/11/2026 - Midday Dunes - Bob Ross Workshop
Thu, Jun 11, 6:00 PM
Claridge · Evolutions Studio
Almost full
6/11/2026 - Midday Dunes - Bob Ross Workshop
Thu, Jun 11, 6:00 PM
Claridge · Evolutions Studio
6/25/2026 - Northern Lights - Bob Ross Workshop
Thu, Jun 25, 6:00 PM
Claridge · Evolutions Studio
6/25/2026 - Northern Lights - Bob Ross Workshop
Thu, Jun 25, 6:00 PM
Claridge · Evolutions Studio
7/2/2026 - Freedoms Flight - Bob Ross Workshop
Thu, Jul 2, 6:00 PM
Claridge · Evolutions Studio
7/2/2026 - Freedoms Flight - Bob Ross Workshop
Thu, Jul 2, 6:00 PM
Claridge · Evolutions Studio
7/16/2026 - Sailor’s Delight - Bob Ross Workshop
Thu, Jul 16, 6:00 PM
Claridge · Evolutions Studio
7/16/2026 - Sailor’s Delight - Bob Ross Workshop
Thu, Jul 16, 6:00 PM
Claridge · Evolutions Studio
8/6/2026 - Autumn Mountain - Bob Ross Workshop
Thu, Aug 6, 6:00 PM
Claridge · Evolutions Studio
8/6/2026 - Autumn Mountain - Bob Ross Workshop
Thu, Aug 6, 6:00 PM
Claridge · Evolutions Studio
8/20/2026 - Meadow Falls - Bob Ross Workshop
Thu, Aug 20, 6:00 PM
Claridge · Evolutions Studio
8/20/2026 - Meadow Falls - Bob Ross Workshop
Thu, Aug 20, 6:00 PM
Claridge · Evolutions Studio
Date Night Sip&Paint
Fri, Jun 12, 6:00 PM
Winchester · 16 S Loudoun St
Date Night Sip&Paint
Fri, Jun 12, 6:00 PM
Winchester · 16 S Loudoun St
Sales end soon
VIP Meet and Greet (General Admission Sold Separately)
Thursday at 8:00 PM
Winchester · Backseat Events USA
Sales end soon
VIP Meet and Greet (General Admission Sold Separately)
Thursday at 8:00 PM
Winchester · Backseat Events USA
Standup Comedy at Escutcheon Brewing! (Winchester, Va)
Fri, Jul 10, 8:00 PM + 1 more
Winchester · Escutcheon Brewing Co.
Standup Comedy at Escutcheon Brewing! (Winchester, Va)
Fri, Jul 10, 8:00 PM + 1 more
Winchester · Escutcheon Brewing Co.
Truss Brewing Summer Comedy Series: Buddy Flip Live
Sat, Jun 27, 7:30 PM
Pleasant Hills · TRUSS Brewing Company
Truss Brewing Summer Comedy Series: Buddy Flip Live
Sat, Jun 27, 7:30 PM
Pleasant Hills · TRUSS Brewing Company
Painting With Purpose: LAST FRIDAYS
Fri, Jun 26, 6:30 PM + 4 more
North Versailles · Painting with Purpose
Painting With Purpose: LAST FRIDAYS
Fri, Jun 26, 6:30 PM + 4 more
North Versailles · Painting with Purpose
Painting with Purpose: LAST FRIDAYZ
Fri, Jun 26, 6:00 PM + 9 more
North Versailles Township · 3206 Maryland Ave
Painting with Purpose: LAST FRIDAYZ
Fri, Jun 26, 6:00 PM + 9 more
North Versailles Township · 3206 Maryland Ave
The 412 Awards Experience
Sun, Jun 28, 9:00 PM
Duquesne · 1016 Duquesne Blvd
The 412 Awards Experience
Sun, Jun 28, 9:00 PM
Duquesne · 1016 Duquesne Blvd
LIVE COMEDY SHOWCASE
Sat, Jun 6, 8:00 PM
Canonsburg · Atomic Comedy Co.
LIVE COMEDY SHOWCASE
Sat, Jun 6, 8:00 PM
Canonsburg · Atomic Comedy Co.
Atomic Comedy Co. Presents Dan Sebree
Fri, Jun 12, 8:00 PM
Canonsburg · Atomic Comedy Co.
Atomic Comedy Co. Presents Dan Sebree
Fri, Jun 12, 8:00 PM
Canonsburg · Atomic Comedy Co.
Atomic Comedy Co. Presents Josh Ritenour
Friday at 8:00 PM
Canonsburg · Atomic Comedy Co.
Atomic Comedy Co. Presents Josh Ritenour
Friday at 8:00 PM
Canonsburg · Atomic Comedy Co.
Atomic Comedy Co. Presents Jake Calvin
Fri, Jun 19, 8:00 PM
Canonsburg · Atomic Comedy Co.
Atomic Comedy Co. Presents Jake Calvin
Fri, Jun 19, 8:00 PM
Canonsburg · Atomic Comedy Co.
Afro P Funk & Poetry
Sun, Jun 7, 7:00 PM
Homestead · The Glitterbox Theater
Afro P Funk & Poetry
Sun, Jun 7, 7:00 PM
Homestead · The Glitterbox Theater
Broadway After Dark (PGH) - Broadway Karaoke & Sing-Along
Mon, Jun 8, 7:00 PM
Homestead · Dave & Buster's Pittsburgh - Homestead
Broadway After Dark (PGH) - Broadway Karaoke & Sing-Along
Mon, Jun 8, 7:00 PM
Homestead · Dave & Buster's Pittsburgh - Homestead

Trends in Oakland

Explore more trends

Explore more trends

Frequently asked questions about Oakland

What are the best events to attend?

According to Eventbrite, the best events are:

Mentalist - Richard Passaro

6/11/2026 - Midday Dunes - Bob Ross Workshop

6/25/2026 - Northern Lights - Bob Ross Workshop

7/2/2026 - Freedoms Flight - Bob Ross Workshop

Which events are currently trending in Oakland?

The trending searches this month in Oakland are:

rebuilding liberty

mothers day brunch

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

VIP Meet and Greet (General Admission Sold Separately)

Atomic Comedy Co. Presents Josh Ritenour

LIVE COMEDY SHOWCASE

Afro P Funk & Poetry