Curated by Joanne Dal Santo
Weekend
Guide
Discover the best events, dining, and outings across Chicagoland and Northwest Indiana. Your local insider picks for every weekend.
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Curated by Joanne Dal Santo
Discover the best events, dining, and outings across Chicagoland and Northwest Indiana. Your local insider picks for every weekend.
Your Local Insider
The Weekend Guide curates the best events, activities, restaurants, and outings across two states: Illinois and Indiana. From Frankfort's forest preserves to Crown Point's downtown square, we dig up the picks so you can skip the search and start your weekend.
Whether you're in Frankfort, Mokena, New Lenox, or Orland Park on the Illinois side, or Dyer, Highland, Munster, or Schererville on the Indiana side, there's always something worth checking out. We cover both states in one place.
Curated by
Associate Broker, @properties. Your local insider for the best of both states.
Featured Picks
Fresh picks for the weekend of Sept 25-27, 2026, with a first look at the first weekends of October. Browse Illinois and Indiana side by side in one place.
Frankfort's 14th Annual Wine & Ale Walk is a 21-and-older afternoon of tastings at downtown businesses with live music on the Breidert Green stage.
Official DetailsNearly 70 vendors gather at Breidert Green every Sunday with produce, baked goods, flowers, honey, and live music on the stage, running through Oct 25.
Official DetailsLemontster Days' 'Stars, Stripes & Scarecrows' scarecrow trail unrolls across downtown Lemont; vote for your favorite as you stroll.
Official DetailsLemont's illuminated pumpkin trail returns to The Forge: Lemont Quarries with a half-mile glowing path of thousands of carved pumpkins plus family-friendly zones, running every night into November.
Official DetailsA South Suburbs fall tradition minutes from Orland Park: pumpkin patch, rides, pig races, a petting zoo, hayrack rides, and celebrity pumpkin displays.
Official DetailsFour days of BBQ food, a beer garden, carnival rides, crafts, and live music at Main Square Park, closing Sunday with the AC/DC tribute Bonfire.
Official DetailsPortage's free Harvest Festival returns to Founders Square with live music, food trucks, a beer garden, games, and local artisan vendors.
Official DetailsThe last market of the season: 70-plus vendors with produce, baked goods, artisan crafts, and live music at Bulldog Park, next to the courthouse square.
Official DetailsThe Sunday farmers market at Centennial Park runs through Oct 11, and the late-season Sundays serve up the best of the fall harvest.
Official DetailsThe Pumpkin Glow Trail lights up thousands of jack-o-lanterns Fridays through Sundays, 6:30-9 p.m., with corn mazes, hayrides, and the pumpkin patch open daily this season.
Official DetailsMore Picks
The Buckley Homestead Fall Festival returns to the Lake County living-history farm in Lowell this October with reenactors, historic crafts, food, and entertainment. The 2026 dates are posted at lakecountyparks.com as they are confirmed.
Market season runs strong across Northwest Indiana. St. John opens Sundays 8 a.m. to 1 p.m. from May 3 through Oct 25 at 9660 Wicker Avenue, and Highland's downtown market gathers Thursday afternoons at 2730 Highway Avenue through the season.
Walk the historic Crown Point square, grab coffee at Sip Coffee House, and explore the shops and restaurants lining Main Street. A perfect low-key Saturday.
Looking Ahead
Verified picks rolling into the first weekends of October, across both states.
A free German celebration at St. John the Evangelist Parish: Fri 5-11 p.m., Sat 1-11 p.m., Sun noon-8 p.m., with German food and beer, polka and folk music, and family fun.
Read the PickA free fall celebration at Bulldog Park with German food, a beer garden, live music, hayrides, and games beneath the courthouse clock tower.
Read the PickMunster's free fall family event at Centennial Park with a pumpkin patch, costumed characters, a candy hunt, and pony rides.
Read the PickA costume-friendly 7.5-mile night bike ride hosted by Highland Parks & Recreation, starting and ending at Main Square Park.
Read the PickThe 34th annual Elvis tribute festival, billed as the last in Portage, fills Woodland Park's Community Building with shows, an ETA contest, and a benefit auction for Special Olympics.
Read the PickA matinee of big band classics from the 1920s through the 40s at Munster's professional Equity theater inside Centennial Park, with Blacklisted opening Oct 25.
Read the PickWoodland Park's haunted hayride runs two spooky weekends from 6:30 p.m. with concessions and food trucks. Cash-only tickets, and it sells out.
Read the PickA free trunk-or-treat morning at Prairie West Park with pumpkin train rides, pumpkin decorating, and a costume parade.
Read the PickA costumed 5K and 2K night run through the woods at the Lake County Fairgrounds, with the Hocus Pocus market alongside.
Read the PickThe 21-and-older Halloween brewfest at Woodland Park's Oakwood Hall: beer samplings, a costume contest, food vendors, and music.
Read the PickDyer's cozy harvest-season gathering, confirmed on the 2026 Indiana Festival Schedule Guide, with details shared by the town as the date nears.
Read the PickSchererville Parks & Recreation's longest-running craft show fills the Community Center and Homan Elementary with handmade gifts and holiday decor.
Read the PickThe Mokena Family Fall Fest brings a carnival, food vendors, a beer tent, and live music to Yunker Farm, with Thursday's free Coco movie at 7 p.m.
Read the PickOrland Park's family favorite at Centennial Park with pony rides, hayrides, barrel-train rides, marshmallow toasting, and games. Registration required.
Read the PickMabel's Market's vintage and handmade street market lines Canal Street in downtown Lemont with 50-plus vendors and live music; $5 admission.
Read the PickTinley Junction Mini Golf goes spooky with a Halloween-decorated course and pumpkin decorating; Friday rounds include a paid pumpkin.
Read the PickCostume hikes along a glowing trail at Plum Creek Nature Center in Goodenow Grove, with spooky stations and s'mores; registration on reconnectwithnature.org.
Read the PickA free family afternoon at the Village Commons Performing Arts Pavilion with live music, craft beer, bounce houses, train rides, face painting, and pumpkin decorating.
Read the PickLocal artisans and makers fill the Tony Bettenhausen Recreation Center with handmade crafts, home goods, and seasonal decor.
Read the PickThe Lemont Park District's free Harvest Fest at its Centennial Campus: trunk-or-treat, food vendors, a beer tent, live music, and hayrides.
Read the PickFrankfort's costume 5K at Breidert Green with a run and walk, a 1-mile kids' fun run in costume, and a youth sprint.
Read the PickThe Beecher Lions Club market returns to Firemen's Park for its 2026 season finale with local produce, baked goods, and crafts.
Read the PickThe village's Halloween Happening for little ones runs on the official Crete events calendar, 11 a.m. to noon, with the library's Retro Movie Fridays nearby.
Read the PickTrunk-or-treat, a haunted trail, and a monster market at Main Park from the Mokena Park District.
Read the PickThe Chamber's Halloween Fest at the Village Commons with trunk-or-treat, a pumpkin party, and a costume contest, plus the free Scarecrow Stroll all October.
Read the PickFamily trick-or-treating through business booths, a magician, and Halloween fun at Harmony Square.
Read the PickStay Connected
Want to know what's happening each weekend? Reach out and Joanne will keep you in the loop with fresh picks for your area.