Art in the Park

An outdoor art exhibition of works by nearly 70 professional artists at Lindendale Park.  Artists from around the country display fine arts in a variety of media.  Highland Art Council organize, plan, and host this event in October. Read More

Breakfast with the Easter Bunny

Enjoy a pancake breakfast, a picture with the Easter Bunny, craft, face painting, and live bunny petting zoo hosted by the Highland Civic Women's Club. Read More

Flugel Fest

Family friendly all day event with Best Wings Contest, Wing Eating Contest, Bags Tournament, live music, Kids Korner,  and additional food & drink vendors.
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Gobble Hobble Fun Run

On Thanksgiving morning start the holiday with a 2 mile fun run/walk at Glik Park so you can enjoy the pumpkin pie later. Read More

Harvest Days

A celebration of history & recognition of the farming community to America's growth held at the Latzer Homestead.  The weekend includes entertainment, demonstrations, children's activities, Parade of Power, and auctions. Read More

Highland Optimist Basketball Shootout

A premier high school basketball event held in January with teams from the bordering states competing throughout the day.  Over the years the Shootout has had nationally ranked teams and numerous players that go on to play college and NBA. Read More

Highland Speedway

A one-quarter, semi-banked clay oval race track that hosts various model car races on Saturday evenings in the spring and summer. Read More

Holiday Home Tour

Tour several decorated homes in Highland to be amazed, inspired, and filled with Holiday Cheer.  The IFBW organizes this event and the proceeds are used towards scholarships and other charities within the community. Read More

Holiday Lighted Parade

The Friday evening after Thanksgiving, the Chamber of Commerce organizes a lighted parade to the downtown Square where Santa lights up the town. Read More

July 4th Fireworks

On July 4th the fun starts with inflatables, food, and drinks.  The fireworks display begins at dusk at Glik Park.  Sponsors needed! Read More


A three day church picnic with a German flair that offers food, drinks, games, entertainment, kid's activities, races, auctions, flea market, and the fun is "in tents." Read More

Madison County Fair

A week of carnival rides, livestock shows, musicians, 4-H exhibits, pageants, and a different event in the arena each evening including a tractor pull, combine derby, demolition derby, and stock car races. Read More

Memorial Highland Biathlon

Held the Saturday of Memorial Day weekend.  The main event is a biathlon that consists of a 5 mile run & a 20 mile bike ride either as a team or individual.  Also available, a 5 mile run and a 2K fun run/walk.  Read More

Muny Band

Enjoy concerts on the Square on Friday evenings throughout the summer starting at 8pm. Read More

PBJ Festivals

On the Square on Fridays from 11:30am  to 1pm throughout the summer.  A variety of local vendors with activities for the children, food for purchase, entertainment, and free pbj sandwiches & popcorn from Parks & Rec dept. Read More


A festival held the 2nd weekend in June at the downtown square with carnival rides, entertaining bands, drink & food vendors, and parade on Saturday & Sunday evening.  This fundraiser is hosted by the Highland Jaycees. Read More

Street Art Festival

Watch thirty or more talented artists create artwork of amazing color, depth, and complexity on the streets - with chalk!  This event also includes food vendors, Kreative Kids Corner, music, beer tasting, and a bags tournament. Read More

Treats on the Streets

The Friday prior to Halloween, kids under 12 can trick or treat in their costumes at the participating businesses throughout Highland. Read More