1 — Tour de Bluffs Bike Ride. 8:30 a.m. Saturday, Prairie du Rocher. Sign up at 7:30 a.m. $20 pre-registration; $25 race day; www.visitprairiedurocher.com/community-events/ Food. Benefits Randolph County Historical Society Creole House.
1 — Lebanon Fall Festival. Saturday, brick street in Lebanon. 100-plus vendors with handmade crafts.
1-2 — French and Indian War Encampment. 10 a.m.-5 p.m. Saturday and Sunday, Fort de Chartres State Historic Site near Prairie du Rocher. 1750s historically dressed Native American, soldier, militia and camp follower re-enactors participate in everyday camp activities.
2 — Clinton County Amazing Race. Saturday, New Baden. Team competition. Information: Suzie at 618-588-3014.
2 — Artifact Identification Day. Noon-4 p.m. Sunday, Cahokia Mounds State Historic Site near Collinsville. Bring artifacts for archaeologists to identify.
7-8 — Belleville Chili Cookoff. 11 a.m.-10:30 p.m. Friday and Saturday, downtown Belleville. Free admission. More than 60 vendors will feature chili, desserts, kabobs and more. Purchase sample bowls of chili and vote for The People’s Choice Award. Music by Fan Fare, Well Hungarians and Queens Boulevard. 4th annual Chili Chase 5K Run/Walk & Kids Pepper Dash starting at 8:45 a.m. East Main and Church streets (registration www.bellevillechili.com). Saturday events include a children’s area and the 10th annual Junior Idol singing contest.
7-9 — Highland Art in the Park. Friday-Sunday, Lindendale Park, Highland. On Friday: 10 a.m.-4 p.m. exhibit set-up; Preview Party for artists, sponsors and VIP guests. Artists displaying and selling thier work. On Saturday: exhibits open, 10 a.m.-5 p.m.; Kids Creations projects continuously, 11 a.m.-3 p.m.; music, art demonstrations, art gallery for kids to buy art. On Sunday: exhibits open, 11 a.m.-4 p.m.; music, art demonstrations, art gallery for kids.
8 — Pumpkinfest. 9 a.m.-4 p.m. Saturday, Courthouse Square, downtown Waterloo. Free. 5K Run/Walk, music, craft and merchant booths, pumpkin painting, pumpkin games, pumpkin contests, washer tournament, demonstrations, face painting, food.
8 — World War II Days. 10 a.m.-5 p.m. Saturday, Fort de Chartres State Historic Site near Prairie du Rocher. Large-scale event featuring World War II-era displays, demonstrations and re-enactments. Co-sponsors: Living History Association and U.S. 2nd Ranger Infantry Battalion of St. Louis.
8 — Car Cruise. 5-9 p.m. Saturday, on the brick street in Lebanon.
9 — Maryville Concert Series. 3 p.m. Sunday, Fireman’s Park on Illinois 159, Maryville. George Portz & Friends of Bluegrass. Free.
15 — Freaky 5 Halloween 5K Run/Walk and Bonfire. 3 p.m. Saturday, Caseyville Park. Registration at 3 p.m., free spinal checks and rock taping. 5K starts at 5 p.m. After-party with food, DJ, bonfire and marshmallows. Registration information at www.caseyville.org
15 — Mascoutah Fall Fest and Chili Cookoff. 10 a.m.-4 p.m. Saturday, downtown Mascoutah. Car show.
16 — Leclaire Parkfest. Noon to 5 p.m. Sunday, Leclaire Park, Edwardsville. Celebration of the Leclaire National Historic District in Edwardsville. Music. Wine and beer garden, food. Local artists display their work. Games for children. Exhibits of historic photos and narrated trolley tours tell the story of the former cooperative village.
18 — Fall Wurstmarkt. Tuesday, St. John EUCC, Collinsville. Pork sausage, sauerkraut, mashed potatoes, butter beans, peas, bread, drinks, desserts.
22 — Salt Lick Point Honeysuckle Day. 9 a.m.-noon, Saturday, Emergency Services Building, 626 S. Meyer Ave., Valmeyer. Learn ways to control invasive bush honeysuckle. Homemade cookies. Free.
23 — Oktoberfest. 2 p.m. Sunday, Hidden Lake Winery, 10580 County Road 400 East, Aviston. George Portz & Friends of Bluegrass. Free.
28 — Halloween Party. 6:30-8:30 p.m. Friday, Caseyville Community Building, 909 S. Main St., Caseyville. Free admission. Game tickets 4 for $1. Hay ride, weather permitting. Costume contest. Halloween picture, $4. Hot dogs, chili, chili dogs, soda and chips provided by Caseyville Fire Auxiliary. Receive one special raffle ticket for can of food or money donation to the Caseyville Food Pantry.
29 — Chili -Soup Cookoff & Cupcake Wars. 3-10 p.m. Saturday, New Baden Village Park. Free admission. Big Six Wheel, craft fair, hayrides, music. Drinks and food available for purchase. Soup, chili and cupcakes served, 3-7 p.m.; all-you-can-eat armbands on sale at 3 p.m. Bonfire, 7 p.m. Awards, 8 p.m. Unlimited children’s activities armbands $5. Presented by New Baden Chamber of Commerce. www.newbadenchamber.com
30 — Halloween Parade and Party. 2 p.m. Sunday, Leu Civic Center, Mascoutah.
30 — Witches’ Night Out. Night of shopping and Halloween fun on the brick street in Lebanon.
31 — EdGlen Chamber of Commerce Halloween Parade. Halloween night, Edwardsville. More than 100 floats, marching bands, school groups and entertainers.