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Fun things to do in the Midwest

Things to do in the Midwest and South Illustration by James Gulliver Hancock

A curated list of the best upcoming events in Illinois, Indiana, Kansas and Missouri.


Hakuna Matata Oktoberfest Dinner Cruise

October 7 See the autumn foliage along the Mississippi River bluffs while dining on German fare such as bratwurst, sauerkraut, roasted chicken, and red cabbage. The 2-hour cruise departs at 4:30 p.m. Tickets are $47. Grafton Harbor, Grafton.

Fort de Chartres Winter Rendezvous & Woods Walk

FREE! November 5–6 Historic re-enactors portraying trappers, soldiers, and early Native Americans will trade goods, participate in a muzzleloader-shooting competition, and more. As you walk through the encampment, you’ll feel as though you’ve stepped back into the frontier era. Fort de Chartres State Historic site, Prairie du Rocher.

Wine & Food Pairing Weekend: Autumn Inspirations

November 5–6 Sample food pairings at each of the 11 Shawnee Hills Wine Trail locations during this celebration of autumn’s bounty. Tickets include a souvenir wine glass and a chance at prizes along the trail. Designated drivers will receive food samples, a nonalcoholic drink at each winery, and the chance to win prizes. Tickets, $35. Southern Illinois.

Belleville Christkindlmarkt

FREE! November 25–December 23 Celebrating its 9th year, Christkindlmarkt has become the most popular holiday shopping event in southwestern Illinois. Modeled after one of Germany’s oldest Christmas markets, the festive event is open Thursdays through Sundays after Thanksgiving, with additional dates during the week before Christmas. Public Square, Belleville.

Santa’s Chocolate Express

December 3 Sample chocolaty treats as you complete your holiday shopping in Grafton’s one-of-a-kind stores. Carolers will provide a festive soundtrack, and you can hop on a shuttle that travels up and down Main Street. Stop at Grove Memorial Park and visit with Santa. Tickets include the shuttle, treats, discounts at Grafton businesses, a holiday wine glass, and more. Tickets, $15 in advance and $20 on the day of the event. Grafton.


Southern Indiana Renaissance Faire’s Celtic Fling

October 15–16 and 22–23. Lords and ladies, experience music, dance, food, and entertainment such as jousting, magic, and falconry over 2 weekends. Arts-and-crafts vendors also will be at the 15th-century-styled village. Admission is $15 for adults and $7 for children 3–12. Birdsell Castle, Charlestown.

Ferdinand Christkindlmarkt

FREE! November 18–20 At the opening ceremony on Friday, a Christmas angel will appear outside the Monastery Immaculate Conception and entertain with her melodious voice. A bell choir and chanting monks will add to the magic. Then on Saturday and Sunday, browse through 6 locations with more than 200 booths selling hand-crafted items, art, jewelry, quilts, candles, and more. Ferdinand.

Christmas Celebration

November 26–December 26 Celebrate the holiday season in the town named after Saint Nick himself during the first 3 weekends in December. See the annual Christmas parade on December 10, roast chestnuts over an open fire, write a letter to Santa, enjoy festive shopping, and drive through the 1.2-mile Santa Claus Land of Lights to see the story of Rudolph told in brilliant LED lights. $15 per car. Santa Claus.



September 24–25 and October 1–2 Celebrate all things autumn at this annual festival that includes a pancake breakfast, music, food, and plenty of freshly-pressed apple cider, apple cider doughnuts, and Lost Trail Root Beer. Vendors will offer a variety of arts and crafts. Activities around the general store are free; admission is $13 for the family farm and gives access to animals, a corn maze, and a pumpkin patch. Louisburg Cider Mill & Country Store, Louisburg.


October 21–29 Since 1919, this festival has been a celebration of Halloween and autumn. Enjoy parades, a carnival, music, and the crowning of Queen Neelah. This year, a theatrical production of Peter Pan is also part of the fun at Neewollah (Halloween spelled backwards). Tickets vary by event. Downtown, Independence.

Third Fridays in Downtown OP

FREE! November 18 On the third Friday of every month, visit downtown Overland Park, where shops and restaurants stay open late for this festive event, with the November theme of “Mayor’s Holiday Festival.” You might happen upon live music or a new exhibit opening in a gallery as you window shop. Make it a date night, a family outing, or a girlfriends’ gathering at this monthly event held from 5–8 p.m. Overland Park.

Holiday Open House at Cider Mill Country Store

FREE! November 26 With the apple harvest complete, the mill’s Country Store is decked out for the season. Enjoy fresh hot apple cider and apple cider donuts as you shop with festive music in the air. Choose from gift baskets and other one-of-a-kind gift items. Louisburg Cider Mill, Louisburg.

Snowglobe Express

November 11–December 23 All aboard the Midland Historic Railway for a 12-mile train ride from the Baldwin City Train Depot to the Snowglobe Christmas Village. Children can deliver letters to Santa in the train’s postal car, which is illuminated and decorated for the holidays. Trips are offered Friday through Sunday in November and every day in December leading up to December 23. Adult tickets start at $35. Baldwin City.

Lawrence Old Fashioned Christmas Parade

FREE! December 3 Horse-drawn carriages adorned in garlands and bells parade down Massachusetts Street to kick off the holiday season in this distinctive event that starts at 11 a.m. Cozy up with hot cocoa and blankets to celebrate American heritage while watching the spectacle. Lawrence.


Art in the Park St. Louis Hills

FREE! September 25 This family-friendly event returns after a 2-year absence to the St. Louis Hills neighborhood. Dozens of artists exhibit and sell their work. Festivalgoers enjoy music and a variety of food and drink. Francis Park, St. Louis.

Roots N Blues Festival

October 7–9 Enjoy a weekend of national and local musical acts, food, drink, crafts, and more. This year’s headliners include Jon Batiste, Chaka Khan, and Tanya Tucker. On Saturday morning, the Betsy Farris Memorial Run honors the former festival director (2009–2016). This is a cashless event. Wristbands are used for admittance and to pay for any purchases at the festival. Tickets range from $64.47 to $136.34. Stephens Lake Park, Columbia.

Dia de los Muertos and a Celebration of Latinx Culture

FREE! November 5–6 Celebrate and remember those we’ve lost with altars at Forest Park’s Missouri History Museum that represent Latin American cultural traditions. This annual event also includes live music, dance performances, an art display, food and drink vendors, and a procession through the park. St. Louis.

St. Charles Christmas Traditions

FREE! November 25–December 24 On Wednesdays and weekends, the brick streets of downtown St. Charles invite guests into the holiday spirit of the past. Encounter legendary figures like Ebenezer Scrooge and Jack Frost as you stroll the festively decorated historic district. From roasted chestnuts to Victorian carolers, it’s a feast for the senses. Scenes from A Christmas Carol come to life on Wednesday evenings. St. Charles.

An Old Time Christmas

November 5–December 30 More than 6.5 million twinkling lights give Branson’s Silver Dollar City a festive glow during this annual celebration. In the theme park’s Midtown area, you’ll be dazzled by animated reindeer, moving trains, stars, snowflakes, and light tunnels. Live shows, seasonal cuisine, a nightly parade, and plenty of shopping opportunities will help you get into the spirit of the season. Free with admission to Silver Dollar City, which starts at $79 for adults. The park is closed on most Mondays and Tuesdays during the festival. Branson.

FREE! indicates free admission to the event, but additional fees may be required. Be sure to designate a driver if you plan to drink alcohol.

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AAA Travel Alert: Many travel destinations have implemented COVID-19–related restrictions. Before making travel plans, check to see if hotels, attractions, cruise lines, tour operators, restaurants, and local authorities have issued health and safety-related restrictions or entry requirements. The local tourism board is a good resource for updated information.

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