Highwood offers a peaceful lakeside escape with easy access to Lake Michigan paddling, forest trails, and bird watching. Perfect for travelers seeking relaxed outdoor fun along the Illinois North Shore.
Highwood offers a peaceful lakeside escape with easy access to Lake Michigan paddling, forest trails, and bird watching. Perfect for travelers seeking relaxed outdoor fun along the Illinois North Shore.
Outdoor Adventure in Highwood, Illinois
Located on Illinois’ scenic North Shore, Highwood is a small town that blends lakefront recreation with nearby forest preserve trails. It’s an excellent spot for outdoor lovers who want quiet access to Lake Michigan and natural areas without the crowds.
Discover the unique natural wonders, summits, and scenic landmarks that make Highwood, Illinois special.
★ 7.8⌖ 13.55 milesExplore Lyons Woods Forest Preserve, perfect for hiking and birdwatching near Waukegan, IL. Enjoy serene trails through lush forests and spot local wildlife. Ideal for nature walks in spring and fall.
★ 7.5⌖ 15.47 milesExplore over 5.5 miles of scenic trails at Rollins Savanna Forest Preserve in Grayslake, IL. Ideal for hiking and birdwatching, it's a serene spot for viewing wildlife. Best visited in spring and fall for vibrant scenery.
Discover the top adventure activities and curated experiences in Highwood, Illinois, verified by our editors to help you make the most of your trip.
Book unforgettable outdoor adventures, guided tours, and gear rentals with verified Local Experts in Highwood, Illinois.
⌖ 3.7 miAn 8-hour guided ice-fishing day on the Fox Chain O’Lakes where professional guides provide heated shanties, rod-and-reel combos and on-ice transport so you can focus on fishing.
⌖ 3.7 miA guided, group-format 4-hour walk-out ice-fishing trip that leads anglers of all skill levels onto the frozen lakes for instruction, gear, and memories.
⌖ 3.7 miA full-service, eight-hour ice-fishing outing run by professional guides — heated shanties, top rods, and on-ice transport let you focus on chasing bluegill, crappie, walleye, or pike.
⌖ 3.7 miA four-hour, guide-led ice-fishing outing on the Fox Chain O’Lakes that supplies shanties, gear and on-ice transport so you can focus on catching crappie, panfish, walleye and bass.
⌖ 4.9 miAn evening outing that pairs a 1.5-hour twilight canoe paddle (departing at 6pm) with a catered dinner, live music and a bonfire — this guide lays out what to expect and how to plan.
⌖ 8.7 miA private, 35‑minute aerial tour operated out of Wheeling that flies a small plane over Chicago’s signature skyline and lakefront icons—this guide distills what to expect and how to prepare.
⌖ 8.9 miA one-hour, beginner-friendly pour-paint session in Aurora where participants pour vibrant paints onto figurines—useful for planning family outings, parties, or a solo creative hour.
⌖ 11.2 miWeekend general‑admission tickets buy a timed, three‑hour window at Kroll’s Fall Harvest Farm for hayrides, a corn maze, animal areas and access to the pumpkin patch and gift shop—this guide explains how to make the most of that limited slot.
⌖ 13.6 miPrivate, captain-operated boat cruises with Oselka Marina ranging from two hours to a full day for parties of up to six passengers.
⌖ 14.7 miRent a roomy 22-foot luxury tri-toon with a 115 hp motor for 4-, 8- or 10-hour outings on the Chain O'Lakes — this guide explains what to expect and how to plan.
⌖ 16.7 miA focused, 105‑minute guided exploration of Uptown’s entertainment heyday and architectural evolution—this guide orients you to the tour’s route, meeting point, and what to bring.
⌖ 17.1 miA short-format guide to a 1–7 day pontoon rental aboard a 20‑foot, 10‑person Landau at Round Lake Park—useful for planning capacity, duration and safety essentials.
⌖ 18.3 miA 30-minute helicopter tour from Heli Chicago that flies past Woodfield Mall, Barrington Hills, the Grand Victoria Casino and along the Fox River — this guide explains what to expect and the essential logistics.
⌖ 18.3 miA 1.5-hour immersive walking tour from the Historic Farnsworth House that examines paranormal encounters, Victorian death rituals, and culminates in a visit to the Farnsworth House cellar.
⌖ 18.7 miA 1.5‑hour SUP Yoga class on Chicago waters led by certified instructor Mary Lou Cerami; this guide explains what to expect, who it suits, and what to bring.
Make the most of your visit to Highwood, Illinois with these essential planning tips, seasonal events, and protected lands.
Highwood, Illinois hosts celebrated events throughout the year showcasing the region's culture, outdoor lifestyle, and community spirit.
Experience the vibrancy and unique outdoor heritage of Highwood, Illinois during the iconic Highwood Beach Music Fest. Plan accommodations and permits early.
Experience the vibrancy and unique outdoor heritage of Highwood, Illinois during the iconic Highwood Art & Craft Fair. Plan accommodations and permits early.
Experience the vibrancy and unique outdoor heritage of Highwood, Illinois during the iconic Lakefront Fishing Derby. Plan accommodations and permits early.
Highwood, Illinois is surrounded by incredible protected natural lands offering pristine trails, wildlife habitats, and wilderness conservation.
Indiana Dunes National Park, located along the southern shore of Lake Michigan, offers a diverse landscape of dunes, wetlands, prairies, and forests and is renowned for its recreational opportunities and vibrant biodiversity.
Kettle Moraine State Forest is a diverse natural area in southeastern Wisconsin known for its unique glacial landforms, rich ecosystems, and extensive recreational opportunities including hiking, mountain biking, and skiing.
Starved Rock State Park in Illinois is renowned for its stunning canyons and waterfalls, offering visitors a unique glimpse into the natural beauty of the Midwest.
Matthiessen State Park, located in central Illinois, offers striking sandstone canyons and abundant outdoor opportunities in a landscape shaped by historic geological forces.
Bring your own kayak or rent nearby for lake paddling activities.
Check local weather for Lake Michigan conditions, especially in spring and fall.
Use nearby forest preserve trail maps to plan hiking and biking.
Parking can be limited near Highwood beach in summer weekends.
Always check local regulations, fire restrictions, trail conditions, and weather forecasts before setting out on any adventure in Highwood, Illinois. Respect nature, wildlife, and fellow adventurers by following Leave No Trace principles.