Paint the Town: En Plein Aire Art Festival
2026-09-11 - 2026-09-13 | Nell’s Woodland, 2000 Alexis Ave., Ottawa, IL, 61350, United States
The City of Ottawa Arts Committee invites you to their second annual Paint the Town: En Plein Air Festival in Ottawa, IL. Plein air artists are invited to use their vision and talents to capture picturesque scenes. Nestled just 80 miles southwest of Chicago, Ottawa, Illinois, is a hidden gem for artists seeking inspiration. With its beautifully landscaped downtown, historic churches, architecture, and vibrant public parks, the city offers a diverse and dynamic backdrop for plein air painters. Framed by the confluence of the Illinois and Fox Rivers, Ottawa boasts breathtaking waterfront views, lush nature preserves, and charming streetscapes, making it the perfect setting for an immersive outdoor painting experience.

Over three days, artists will have the opportunity to explore, create, and compete for $5,000 in prizes graciously donated by Bob and Cheryl Nelson, while connecting with fellow artists and art lovers in a welcoming, inspiring environment.

Whether you’re drawn to the rich textures of historic architecture, the soft light reflecting off the river, or the serenity of our natural landscapes, Ottawa has a scene for every artistic vision. Come paint with the Arts Committee and let the town become your canvas!

Event Schedule

Friday, September 11 – Town Tours
• Get inspired and discover Ottawa’s most scenic spots before painting begins!
• Two guided bus tours are available
• Tours will highlight historic sites, hidden gems, and ideal painting locations

Saturday, September 12 – Paint the Town
• All-day painting begins
• Artists may set up anywhere within the Ottawa city limits to paint en plein air

Sunday, September 13 – Awards Exhibition at Nell’s Woodland
• 8:00 AM – All completed artwork must be turned in for judging
• 10:00 AM – Awards Exhibition & Winner Announcements, and Easel Sales
• 11:00 AM Nell’s Woodland Arts Day, including activities, demonstrations, and food!

Awards & Prizes ($5,000 Total Prize Pool)
• Best in Show — $2,000
• 2nd Place — $1,000
• 3rd Place — $600
• 4th Place — $400
• 4 × Judge’s Choice — $250 each

Farmers and Makers Market
2026-09-12 08:00 - 12:30, 2026-09-19 08:00 - 12:30, 2026-09-26 08:00 - 12:30, 2026-10-03 08:00 - 12:30, 2026-10-10 08:00 - 12:30, 2026-10-17 08:00 - 12:30 (America/Chicago) | Jackson St, Ottawa, IL, 61350, United States
Hosted by the Ottawa Area Chamber of Commerce, the Ottawa Farmers & Makers Market is a vibrant, family-friendly event that brings together local growers, makers, and artisans in the heart of downtown Ottawa, Illinois.

Location: Jackson Street, south side of Washington Square Park(Barricades will block access at LaSalle Street and Columbus Street)
Market Hours: Saturdays from 8 am-12:30 pm.

Rusty Halo Autumn Harvest
2026-09-12 09:00 - 16:00, 2026-09-13 09:00 - 16:00 | Rusty Halo, 3277 E. 18th Road, Ottawa, IL 61350, Ottawa, IL, 61350, United States
Enjoy the unique shopping experience set against the backdrop of a 1920s town. More details TBA!

Ottawa's Third Friday Maker's Market
2026-09-18 17:00 - 21:00 | Madison Street
Arts’ culture and entertainment come alive in downtown Ottawa, IL every Third Friday of the month May – September!

Runway to a Cure 5k
2026-09-19 07:00 - 09:30 | Skydive Chicago, 3215 E. 1969th Road, Ottawa, IL, 61350, United States
The 5K will take place on Skydive Chicago’s runway. Skydive is also offering a survivor lap at no charge. Families are welcome to walk/run.

All proceeds are going towards the Northwest Hospital Cancer Research Fund.

Skydive Chicago is also looking for a few sponsors to help with water stations and the timing system.

Walk to End Alzheimers
2026-09-26 08:30 - 11:00 | Jordon Block, 101-123 W Main St 61350, Ottawa, IL, 61350, United States
Festivities Begin at 8:30am
Ceremony at 9:30am
Walk at 10:00am
For registration and donation information, check out the Walk’s page
More details TBA.

Ottawa Fall Fest & Parade 2026
2026-10-04 08:00 - 17:00 | Downtown Ottawa
More details TBA!

Out of the Darkness Walk
2026-10-10 11:00 - 13:30 | Washington Square Park, 100 West Jackson St, Ottawa, IL, 61350, United States
At the LaSalle County Out of the Darkness Walk, attendees can walk together to raise awareness, support one another, honor and remember loved ones, and fund critical efforts to protect mental health and prevent suicide.

A Victorian Haunting
2026-10-24 14:00 - 20:00 | Downtown Ottawa
Take a step back in time with the Ottawa Downtown Association and experience a night of shadows, suspense, and intrigue…

2026 Wine & Art Walk at Heritage Harbor
2026-11-07 14:00 - 18:00 | Heritage Harbor Ottawa, 2 Great Loop, Ottawa, IL, 61350, United States
The Wine & Art Walk invites guests to stroll through Heritage Harbor while enjoying local art, wine tastings, and scenic waterfront views. Along a self-guided route, visitors can explore one-of-a-kind artwork from talented local artists, sample a variety of wines and spirits, and soak in the creative energy and charm of the Harbor community. More details TBA!

Rusty Halo Snowman Express
2026-11-14 09:00 - 16:00, 2026-11-15 09:00 - 16:00 | Rusty Halo, 3277 E. 18th Road, Ottawa, IL 61350, Ottawa, IL, 61350, United States
Enjoy a unique shopping experience set in the backdrop of a 1920s town. More details TBA!

Festival of Lights Parade
2026-11-27 18:00 - 20:00 | Downtown Ottawa
Kick off the holiday season in dazzling style at Ottawa’s beloved Festival of Lights Parade! Join us in the heart of downtown as festive floats, sparkling lights, and holiday music fill the streets with cheer. This magical tradition brings families and friends together to celebrate the season, with a joyful procession that lights up the night and hearts alike.

Bundle up, bring the cocoa, and make your way downtown for a holiday experience you won’t want to miss!

Freezin' for a Reezin' 2026
2026-12-04 07:30 - 17:00 | IL

A Very Merry Harbor Christmas
2026-12-05 08:00 - 17:00 | Heritage Harbor Ottawa, 2 Great Loop, Ottawa, IL, 61350, United States
A Very Merry Harbor Christmas transforms Heritage Harbor into a festive holiday wonderland filled with twinkling lights, seasonal cheer, and family-friendly activities. Guests can enjoy visits with Santa and Mrs. Claus, horse-drawn carriage rides, holiday shopping, and the warmth of bonfires, all culminating in the beloved lighting of the Harbor Christmas tree to celebrate the start of the holiday season. More details TBA!

Penguin Plunge
2027-01-30 11:00 - 15:00 | Skydive Chicago, 3215 E. 1969th Road, Ottawa, IL, 61350, United States
