Record Roundup: 25+ opportunities for fall fun in the North Shore

The temperature is dropping and the leaves are getting ready to turn — just in time for a wealth of seasonal activities across the North Shore. 

Take stock of the plethora of fall and Halloween events in your area with this roundup of festivals, family-friendly bashes, costumed-skates and more. 

We miss something? Let us know at newsroom@therecordns.org.

JUMP TO: WINNETKA | WILMETTE | HIGHLAND PARK | GLENCOE | NORTHFIELD | KENILWORTH

Winnetka

Fall Fest: 4-7 p.m. on Sept. 27, Skokie Playfield, 540 Hibbard Road

Winnetka’s annual Fall Fest will feature food trucks, music from an interactive DJ, and alcoholic beverages. Adult admission is free but children must obtain a $20-$25 wristband to take advantage of a plethora of games, inflatables, face painting, a petting zoo, hayride and pony rides. 

Family Campfire: 6-7:45 p.m. on Oct. 10, Crow Island Woods, 1140 Willow Road

Families looking to relax together around a campfire, roasting hot dogs and s’mores to the tune of instrumental folk music, can register online for $10-$15. The Winnetka Historical Society will also offer informational walk-throughs to the local log cabin. 

Pumpkins in the Woods: 4-6 p.m. on Oct. 24, Hubbard Woods Park, 939 Old Green Bay Road

The Winnetka Park District will transform Hubbard Woods Park into a pumpkin patch for this fall event, one replete with pumpkin decorating, carnival games, bounce houses, a DJ and Halloween costume contest. Families must register online for $5-$7 to receive a pumpkin and decorations. Costume contest registration will begin at 4:30 p.m. and feature most original, scary and funny categories.

Halloween Party on Ice: 10:30 a.m.-12 p.m., Oct. 25, Winnetka Ice Arena, 490 Hibbard Road 

Don your best Halloween costume and lace up your ice skates to glide around to some spooky music at Winnetka’s ice rink. Admission is $2 per skater and skates are available for rent at $4. No costume masks covering the entire face will be allowed in. 

Wilmette

North Shore Artisan Market: 10a.m.-4p.m., Sept. 13-14, Wilmette Station, 722 Green Bay Road 

After first launching in Northbrook last year, the North Shore Artisan Market has expanded to downtown Wilmette. The fall market will reportedly feature “100 talented artisans” in food, fashion, art and home goods. The celebration of small and local businesses will also be easily accessible from the Wilmette Metra station. 

Wicked Wilmette: 5:30-7:30 p.m., Oct. 17, Lakeview Center at Gillson Park, 800 Gillson Park Drive

This year’s Wicked Wilmette event has relocated because of construction at Hibbard Park but will still include a range of activities like face painting and hay rides. “Spooky Stations”  throughout the park will give away treats, and a pumpkin patch will feature a decorating station. Costumes are encouraged. Registration is required for children only and costs $26 for residents, $32 for nonresidents. 

Spooky Skate: 1-2:30 p.m., Oct. 26, Centennial Ice Rinks, 2300 Old Glenview Road

Take to the ice for a spooky public skate session in Wilmette that will include games, a costume contest and more. Entry is $5 for those in costume or free for those 5 years old and under and in costume. Otherwise, entry is $4 for those 5 years old and under, $8 for students and $9 for adults. Rental skates will be available. 

Wilmette Children’s Theater fall production: ‘Elf the Musical Jr.’: Nov. 7-16, Community Recreation Center, 3000 Glenview Road

Tickets will go on sale starting at 10 a.m. on Oct. 21 for the local children’s theater’s production of “Elf the Musical Jr.” The shows will then run for two weekends in November: Nov. 7-9 and Nov. 14-16. Limited seating is available so order online or at the Community Recreation Center’s front desk. 

Highland Park

Oktoberfest in the Ravinia District: 10 a.m.-10 p.m., Sept. 20, Jens Jensen Park, 486 Roger Williams Ave.

Highland Park’s fifth annual celebration of German beer, food and Bavarian music will kick off with the city’s first official BBQ contest. Other festivities to the day-long event will include dancing, live entertainment, Oktoberfest games like a stein-holding contest and family-friendly activities. Entrance is free.

Scarecrow Fest & Downtown Concert: 4-8 p.m., Sept. 26, Port Clinton Square, 600 Central Ave.

Send off this year’s downtown concert series with a festive fall afternoon that will include live scarecrow puppets and live music at Port Clinton Square. Four different bands will perform: Mary Macaroni, Istvan & His Imaginary Band, Ben Tatar & the Tatar Tots and Saturday June Band. More than 24 festive scarecrows decorated by local businesses can be found scattered throughout downtown Highland Park. Check online here for a schedule of the performances and pictures of last year’s scarecrows. 

Highland Park Hoe Down: 11 a.m.-1 p.m., Sunset Woods Park, 1801 Sunset Road

Looking for something new to do this fall season? Highland Park’s inaugural hoe down will provide an afternoon of live music from a local band, activities via lawn games and grub from food trucks. The Big Rigs & Boots will highlight trucks and tractors earlier in the day from 9:30-11:30 a.m. Habitat for Humanity will be on hand as will a fun composting event. Entrance is free and for all ages. 

Stews & Brews: 5-9 p.m., Oct. 11, Port Clinton Square, 600 Central Ave.

Downtown Highland Park’s fourth annual Stews & Brews festival will once again feature plenty of comfort foods and hot beverages for this fall season. On tap will be a range of craft beers, spiced wines, hot toddies and mulled ciders, just as there will be a range of chilis, pozoles, stews, stroganoffs, goulash, pot pies and warm soups. Live music will also be present at this free, all-ages event. 

Pick and Paint Pumpkin Quest: 10-11 a.m., Oct. 16, Heller Nature Center, 2821 Ridge Road

Walk through one of Highland Park’s mini pumpkin patches and select a gourd to decorate with city-provided craft supplies like paint, stickers, and googly eyes. Registration is required at $15 per child (ages 2-5) for residents and $18 for nonresidents. 

Fall Skating Exhibition: 5-6:30 p.m., Oct. 24, Centennial Ice Arena, 3100 Trail Way

Attend this figure skating showcase from young skaters in the Highland Park District’s Learn to Skate program. Entrance is free and those interested in joining in the next fall session, which runs from Oct. 20 to Dec. 18, can email Deb Jenssen at djenssen@pdhp.org for information.

Halloween Candy Stroll: 3:30-5 p.m., Jens Jensen Park, 486 Roger Williams Avenue

The city’s annual candy stroll will have fall activities and participating businesses handing out candy available in the Ravinia District at Jens Jensen Park. Attendance is free. 

Scary Halloween Miniature Golf: 9 a.m.-5 p.m., Oct. 25, River’s Edge Mini Golf, 2205 Skokie Valley Rd.

Interested in some family fun on the miniature golf range? Come in-costume and receive a free round at River’s Edge 18-hole course. No registration is required. The first nine holes are ADA accessible.

Trunk or Treat: 3:30-5 p.m., Oct. 30, Hidden Creek AquaPark, 1220 Fredrickson Place

Those less inclined to go door to door this Halloween can still celebrate the season with a family-friendly Trunk or Treat event hosted by park district staff and local community groups in Highland Park. Kids ages 2 and up and accompanied by a registered adult are invited to go car to car while decorated trunks hand out candy. Costumes are encouraged; entry is free. 

Dia De Los Muertos: 1-3 p.m., Nov. 1, Park Fitness, 1207 Park Avenue West

Join in on an all-ages celebration of traditional dance performances, live music and hands-on craft activities at Highland Park’s Day of the Dead holiday event. The event is free, requires no registration, and will feature sugar skull face painting. Those interested in contributing to the community altar, or ofrenda, to honor a loved one can contact Jessica Soto at jsoto@pdhp.org for information. 

Highwood

Great Highwood Pumpkin Fest: Oct. 2-Oct. 5, Downtown Highwood, 17 Highwood Avenue

Highwood’s 15th annual Pumpkin Festival will put on three full days of live music and include loads of family friendly activities like costume and pumpkin pie eating contests. Check out seasonal-themed installations of skeletons, pumpkin carving stations and a range of food and art vendors. Carnival rides will kick off the event on Oct. 2 in the Highwood Metra Station parking lot, and three different stages will be located on North Avenue, Highwood Avenue and Everts Park. 

Trick or Treat Trek: 3-6 p.m., Oct. 24, Downtown Highwood, 17 Highwood Avenue

This free, family friendly event invites children in costumes to trick-or-treat in downtown Highwood at participating businesses. Traditionally kicking off at the Bank of Highwood – Fort Sheridan and presented by the Highwood Chamber of Commerce, attendees can then look for signs of local shops handing out candy. Check back online in October for more information on all participating businesses.

Glencoe

Bier on the Pier: 4 p.m., Glencoe Beach, 160 Hazel Ave.

This fall celebration will have plenty of live music, locally brewed craft beer, snacks and nice views on deck. Only those 21 and up can enter and registration costs $20 for residents, $25 for nonresidents. Advance registration online here is encouraged as limited tickets may be available day-of at the door. 

Boo Bash: 5 p.m., Takiff Center, 999 Green Bay Road

The Glencoe Park District will transform its Takiff Center into a Halloween-themed playground where kids can trick-or-treat, watch performances and join in on seasonal activities. Costumes are encouraged, as is walking or carpooling since parking is limited. Registration is required once per group. 

Halloween Hello: 10 a.m.-5 p.m., Oct. 31, Downtown Glencoe, 675 Village Court

The Village of Glencoe will have lots on offer this Halloween, with trick-or-treating at participating downtown businesses — which will be clearly demarcated with a “Halloween Hello” sign in their window — and a Ghosts in the Garden event put on by the Glencoe Historical Society in a decorated Eklund Garden. Village Hall will also have a special treat on offer. 

Community Garden Pumpkin Smash: 10:30 a.m., Nov. 8, 380 Old Green Bay Road

Want an environmentally friendly and fun way to toss your pumpkin after Halloween is over? Come to this Glencoe community garden to smash the pumpkins for compost. The event is free and welcome to all ages. 

Turkey Time Bingo: 6 p.m., Nov. 14, Takiff Center, 999 Green Bay Road

This family-friendly event will put on 10 bingo games with an assortment of “wacky prizes.” Entrance is free and all ages are welcome, though space is limited on a first-come, first-served basis. 

Turkey Chase: 4 p.m., Nov. 21, Takiff Center, 999 Green Bay Road

This year’s turkey fun-run will start at Ravine Bluffs Park and continue north along the Green Bay Trail. All ages are welcome at this free event, though the run is designed for young children and advance registration is encouraged. Children must be accompanied by an adult. 

Northfield

Boo Bash: Oct. 24, Willow Park, 401 Wagner Road

This Halloween party will feature games, crafts, a balloonist and a train ride through the park for kids ages 3 to 8. Attendees are encouraged to bring a treat bag and wear costumes. Children must be accompanied by an adult. 

Kenilworth

Historical Society Walking Tour: 1:30 p.m., Sept. 21 and Oct. 12, Kenilworth Train Station, 400 Richmond Road

The Kenilworth Historical Society is hosting two more walking tours this fall in partnership with the Chicago Architecture Center. This year’s new route will focus on homes designed by Frank Lloyd Wright, George Maher and Franklin Burnham located south of Kenilworth Avenue and east of the railroad tracks. The tour is two-hours long and tickets are available online at $10 for members of the historical society.

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