Best events in
Oakland

There's a friendly, local spirit behind the events and things to do in Oakland, IL. The local scene often revolves around community gatherings and seasonal celebrations that bring people together. Exploring the area reveals everything from family-friendly fairs to intimate live music performances in nearby spots.

Much of the activity centers around community-focused gatherings, from local fundraisers to public celebrations.
Find food and drink events that showcase local flavors and craft producers from the region.
Look for live music and performances hosted in intimate settings and local halls.

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Nearby cities

Mahomet

41 miles away

Champaign

33 miles away

Terre Haute

36 miles away

Urbana

33 miles away

Effingham

46 miles away

Marshall

26 miles away

Paris

18 miles away

Danville

39 miles away

Rantoul

44 miles away

Tuscola

17 miles away

Robinson

48 miles away

Monticello

39 miles away

Long Creek

46 miles away

Decatur

49 miles away

Mattoon

23 miles away

Teutopolis

43 miles away

Covington

47 miles away

Rockville

43 miles away

Mahomet

41 miles away

Champaign

33 miles away

Terre Haute

36 miles away

Urbana

33 miles away

Effingham

46 miles away

Marshall

26 miles away

Paris

18 miles away

Danville

39 miles away

Rantoul

44 miles away

Tuscola

17 miles away

Robinson

48 miles away

Monticello

39 miles away

Long Creek

46 miles away

Decatur

49 miles away

Mattoon

23 miles away

Teutopolis

43 miles away

Covington

47 miles away

Rockville

43 miles away

Online Events

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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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The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

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REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

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Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

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Diriger dans l’incertitude : réconcilier performance ET humanité

Tue, Nov 17 • 12:00 PM EST

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

Thu, Nov 5 • 1:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

The Walrus Talks at Home: Canada After America

Thu, Nov 12 • 7:00 PM EST

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

Gestion de l’anxiété dans le traitement des troubles alimentaires

Fri, Nov 13 • 1:00 PM EST

Check ticket price on event

Diriger dans l’incertitude : réconcilier performance ET humanité

Tue, Nov 17 • 12:00 PM EST

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

Check ticket price on event

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Events near Oakland

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Ashmore Estates Public Investigation

Friday • 7:00 PM

Ashmore Estates

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Bella Vita Oct / Festival Family Fun, Forbidden Forest, Mad Gasser Hideout

Friday • 5:00 PM + 1 more

Bella Vita Private Resort

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Ruben Ramirez live at The Castle

Fri, Nov 20 • 8:00 PM

The Castle

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Tom Arnold at the Harlan Hall Opera House

Sat, Dec 12 • 8:00 PM

Harlan Hall

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Next Stop Comedy at Hometown Grounds Coffee and Events! - Tuscola, IL

Sat, Jan 23 • 8:00 PM

Hometown Grounds Coffee and Events

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Investigate Day and /or Night with The Wraith Chasers

Sat, Apr 10 • 12:00 PM

Ashmore Estates

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ELVIS MEETS THE BEATLES TRIBUTE SHOW LIVE AT HARLAN HALL (Marshall, IL)

Sat, Apr 17 • 7:00 PM

Harlan Hall

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Ashmore Estates Public Investigation

Friday • 7:00 PM

Ashmore Estates

Check ticket price on event

Bella Vita Oct / Festival Family Fun, Forbidden Forest, Mad Gasser Hideout

Friday • 5:00 PM + 1 more

Bella Vita Private Resort

Check ticket price on event

Ruben Ramirez live at The Castle

Fri, Nov 20 • 8:00 PM

The Castle

Check ticket price on event

Tom Arnold at the Harlan Hall Opera House

Sat, Dec 12 • 8:00 PM

Harlan Hall

Check ticket price on event

Next Stop Comedy at Hometown Grounds Coffee and Events! - Tuscola, IL

Sat, Jan 23 • 8:00 PM

Hometown Grounds Coffee and Events

Check ticket price on event

Investigate Day and /or Night with The Wraith Chasers

Sat, Apr 10 • 12:00 PM

Ashmore Estates

Check ticket price on event

ELVIS MEETS THE BEATLES TRIBUTE SHOW LIVE AT HARLAN HALL (Marshall, IL)

Sat, Apr 17 • 7:00 PM

Harlan Hall

Check ticket price on event

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Frequently asked questions about Oakland

Where can I find free events in Oakland, IL?

Free events often take the form of public park gatherings and community-sponsored celebrations. Look for seasonal fairs, holiday markets, and local library programs that are open to everyone.

What are some family-friendly things to do in the area?

The area offers many family-friendly events centered on community and outdoor fun. This includes local school functions, park district activities, and seasonal festivals in the surrounding region.

How can I find live music events near Oakland?

Live music can often be found at local bars, community halls, or as part of larger town festivals. These performances typically feature local and regional artists in a relaxed, intimate atmosphere.

Are there places for comedy shows nearby?

Stand-up comedy events are more likely to be found in larger towns in the vicinity. Check performance venues and bars in the broader area for open mic nights or touring comedy acts.

What kind of food and drink events happen in the Oakland, IL area?

Food and drink events often highlight regional producers and local eateries. Expect farmers' markets, seasonal food festivals, and special tasting events hosted by businesses in the area.

Does Oakland have a nightlife scene?

Nightlife in the area is typically low-key, centering on local pubs and community social events. For more active nightlife, exploring the larger cities in the region is a common approach.

Can you suggest some date night event ideas?

A great date night could involve a special dinner event at a local restaurant or catching a performance. Many couples also enjoy attending seasonal festivals or workshops offered in the region.

What opportunities are there for art and culture events?

Cultural events often include craft fairs and showcases by local artisans. Keep an eye out for exhibitions at community centers or pop-up galleries that celebrate regional talent and creativity.

Trending searches

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6. Holiday market

7. Ghost tours

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9. Comedy

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Nearby cities

Mahomet

Champaign

Terre Haute

Urbana

Effingham

Marshall

Paris

Danville

Rantoul

Tuscola

Robinson

Monticello

Long Creek

Decatur

Mattoon

Teutopolis

Covington

Rockville

Mahomet

Champaign

Terre Haute

Urbana

Effingham

Marshall

Paris

Danville

Rantoul

Tuscola

Robinson

Monticello

Long Creek

Decatur

Mattoon

Teutopolis

Covington

Rockville

Online Events

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

Lean Global Connection 2026

The Walrus Talks at Home: Canada After America

REVISED Cottage Food Safety Statewide Online Training

Gestion de l’anxiété dans le traitement des troubles alimentaires

Diriger dans l’incertitude : réconcilier performance ET humanité

The MI5 Archive: Official Secrets

Washington Crossing the Delaware / The Crossing - Film History Livestream

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

Lean Global Connection 2026

The Walrus Talks at Home: Canada After America

REVISED Cottage Food Safety Statewide Online Training

Gestion de l’anxiété dans le traitement des troubles alimentaires

Diriger dans l’incertitude : réconcilier performance ET humanité

The MI5 Archive: Official Secrets

Washington Crossing the Delaware / The Crossing - Film History Livestream

Events near Oakland

Ashmore Estates Public Investigation

Bella Vita Oct / Festival Family Fun, Forbidden Forest, Mad Gasser Hideout

Ruben Ramirez live at The Castle

Tom Arnold at the Harlan Hall Opera House

Next Stop Comedy at Hometown Grounds Coffee and Events! - Tuscola, IL

Investigate Day and /or Night with The Wraith Chasers

ELVIS MEETS THE BEATLES TRIBUTE SHOW LIVE AT HARLAN HALL (Marshall, IL)

Ashmore Estates Public Investigation

Bella Vita Oct / Festival Family Fun, Forbidden Forest, Mad Gasser Hideout

Ruben Ramirez live at The Castle

Tom Arnold at the Harlan Hall Opera House

Next Stop Comedy at Hometown Grounds Coffee and Events! - Tuscola, IL

Investigate Day and /or Night with The Wraith Chasers