Best events in
Monticello

Events and things to do in Monticello, IL, are rooted in its strong sense of community and local charm. The social calendar is marked by annual festivals downtown and seasonal activities at Allerton Park. From live music at a local brewery to scenic train rides, there is a distinctly local feel to most outings.

Stroll through the downtown area around the Historic Courthouse Square, which hosts annual events like Monticellobration FestiFall and the Chocolate Fantasy.
Explore the expansive grounds of Allerton Park and Retreat Center, a popular spot for outdoor concerts and guided hikes.
Catch live music performances at local spots like 3Ravens Food & Spirits or enjoy a craft beer at Monarch Brewing Company.

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Events near Monticello

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Wednesday • 6:30 PM

Gallery art bar

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2026 CU Folk & Roots Festival

Thursday • 5:00 PM

Urbana

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Japan House Fall Open House - Japan House's Past, Present, and Future

Saturday • 11:00 AM

Japan House

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Mahjong & Mocktails : American Mahjong 102: Guided Play

Tue, Oct 13 • 6:00 PM

Farren's at The Inman

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60th Anniversary Celebration of Three Hierarchs Greek Orthodox Church

Sat, Oct 17 • 6:30 PM

I Hotel & Illinois Conference Center

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yellow and Co. presents Dueling Pianos by Twilight Tunes Dueling Pianos!

Fri, Oct 23 • 7:00 PM

Yellow & Co.

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Owl Night

Wed, Oct 28 • 6:00 PM

Allerton Park & Retreat Center

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Executive Director Leadership Network- Peer to Peer Support Lunch

Thu, Dec 10 • 11:30 AM

Community Foundation Of East Central Illinois

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SPEED DATING: MEN SIGN UP

Wednesday • 6:30 PM

Gallery art bar

Check ticket price on event

2026 CU Folk & Roots Festival

Thursday • 5:00 PM

Urbana

Check ticket price on event

Japan House Fall Open House - Japan House's Past, Present, and Future

Saturday • 11:00 AM

Japan House

Check ticket price on event

Mahjong & Mocktails : American Mahjong 102: Guided Play

Tue, Oct 13 • 6:00 PM

Farren's at The Inman

Check ticket price on event

60th Anniversary Celebration of Three Hierarchs Greek Orthodox Church

Sat, Oct 17 • 6:30 PM

I Hotel & Illinois Conference Center

Check ticket price on event

yellow and Co. presents Dueling Pianos by Twilight Tunes Dueling Pianos!

Fri, Oct 23 • 7:00 PM

Yellow & Co.

Check ticket price on event

Owl Night

Wed, Oct 28 • 6:00 PM

Allerton Park & Retreat Center

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Executive Director Leadership Network- Peer to Peer Support Lunch

Thu, Dec 10 • 11:30 AM

Community Foundation Of East Central Illinois

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Online Events

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How To Be Kind To Yourself - Shahroo Izadi

Wed, Oct 14 • 7:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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

Sat, Oct 17 • 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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Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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How To Be Kind To Yourself - Shahroo Izadi

Wed, Oct 14 • 7:00 PM GMT+1

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HBR Press Webinar: Resilient Optimism

Thu, Oct 15 • 8:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thu, Oct 15 • 1:00 PM GMT+1

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

Sat, Oct 17 • 9:00 AM EDT

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

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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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Frequently asked questions about Monticello

What are some family-friendly events in Monticello?

The Monticello Railway Museum offers scenic train rides for all ages. These excursions run on weekends from May through early October. For other fun, look for community events and kids' activities at the annual Monticellobration FestiFall downtown.

Where can I find live music events in Monticello?

Local pubs and breweries are the main spots for live music. Check for performances at 3Ravens Food & Spirits or Monarch Brewing Company. Allerton Park also hosts occasional outdoor concerts on its grounds, offering a scenic backdrop for shows.

Are there food and drink festivals in Monticello?

Yes, Monticello hosts several annual food and drink-themed events downtown. Look for The Whites of Spring for wine sampling and Chocolate Fantasy in the early winter. The weekly Monticello Main Street Farmer's Market also features local food vendors.

How can I experience the outdoors in Monticello?

Allerton Park and Retreat Center is a top destination for outdoor activities. The park features extensive hiking trails, formal gardens, and outdoor sculptures. It also hosts events like concerts and guided nature walks throughout the year.

What kind of events happen in downtown Monticello?

Downtown Monticello's Historic Courthouse Square is a hub for community gatherings. The area hosts annual celebrations like Monticellobration FestiFall and seasonal events like Chocolate Fantasy. It is also the site of the weekly Main Street Farmer's Market.

Which local attractions in Monticello are good for a date?

A scenic train ride at the Monticello Railway Museum makes for a unique outing. For a more traditional evening, consider catching a local production at the Monticello Theatre Association or enjoying drinks at Monarch Brewing Company in its restored church setting.

Does Monticello have a local theatre scene?

Yes, the Monticello Theatre Association is the community's local stage. The group puts on various play productions throughout the year. It's a great way to support local talent and see a show close to home.

What's the best way to find free things to do?

Visiting the Monticello Main Street Farmer's Market is a great free activity. It runs weekly from spring to fall. Also, many of the downtown festivals, like Monticellobration FestiFall, have free-to-attend components like parades and car shows.

Events near Monticello

SPEED DATING: MEN SIGN UP

2026 CU Folk & Roots Festival

Japan House Fall Open House - Japan House's Past, Present, and Future

Mahjong & Mocktails : American Mahjong 102: Guided Play

60th Anniversary Celebration of Three Hierarchs Greek Orthodox Church

yellow and Co. presents Dueling Pianos by Twilight Tunes Dueling Pianos!

Owl Night

Executive Director Leadership Network- Peer to Peer Support Lunch

SPEED DATING: MEN SIGN UP

2026 CU Folk & Roots Festival

Japan House Fall Open House - Japan House's Past, Present, and Future

Mahjong & Mocktails : American Mahjong 102: Guided Play

60th Anniversary Celebration of Three Hierarchs Greek Orthodox Church

yellow and Co. presents Dueling Pianos by Twilight Tunes Dueling Pianos!

Owl Night

Executive Director Leadership Network- Peer to Peer Support Lunch

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Nearby cities

Champaign

Mahomet

Urbana

Decatur

Normal

Paxton

Bloomington

Warrensburg

Long Creek

Fisher

Savoy

St. Joseph

Rantoul

Philo

Lincoln

Tuscola

Villa Grove

Forsyth

Mattoon

Charleston

Illiopolis

Catlin

Oakwood

Champaign

Mahomet

Urbana

Decatur

Normal

Paxton

Bloomington

Warrensburg

Long Creek

Fisher

Savoy

St. Joseph

Rantoul

Philo

Lincoln

Tuscola

Villa Grove

Forsyth

Mattoon

Charleston

Illiopolis

Catlin

Oakwood

Online Events

How To Be Kind To Yourself - Shahroo Izadi

HBR Press Webinar: Resilient Optimism