Top 15 Things To Do in Highwood, Illinois

Why Highwood Belongs on Your Great-Lakes Weekend List

Highwood is compact in miles but generous in options. A five-minute walk separates a downtown coffee shop from a lakeside slip, and that short distance encapsulates the town’s particular appeal: you can launch a morning kayak, swap tales with a local angler over lunch, and spend the golden hour photographing sailboats against a low, silver sun. Boat tours and boat rental operators work the same shoreline access points, so whether you want the ease of a guided sightseeing tour or the hands-on freedom of piloting your own skiff, Highwood makes both simple and scenic. Water activities here are approachable—paddleboarding and kayak rentals often run on hourly schedules, making them perfect for travelers with tight itineraries who still want an up-close encounter with open water.

Beyond the shoreline, Highwood’s human-scale streets beg to be explored on foot or by bike. City tours and walking tours thread the town’s history—think lakeside leisure, Midwestern summer festivals, and an architecture dotted with small theaters and converted industrial buildings. Rent a bike from a local shop and turn a short spin into a bike tour that hits the lakefront, the nearby marshes, and a string of neighborhood parks. Photography tours are a natural fit here; the contrast of water, weather, and old-town facades produces strong light and subject variety from dawn through dusk.

Fishing is woven into the town’s rhythm: families cast from piers, and boats head out for nearshore spots when conditions cooperate. For travelers who prefer guided confidence to DIY, a fishing charter or a guided kayak-fishing outing is an easy way to learn local patterns without guessing at launch points or tides. If you’re visiting in winter, Highwood’s tempo changes—there are fewer boat tours, but winter activities still draw the adventurous: crisp shoreline walks, birding along the lake, and seasonal events that reward bundled-up exploration.

What keeps people coming back is the balance between action and ease. You can notch a morning sail, hop off to explore a neighborhood gallery, and bookend the day with a sunset photography session from a bluff or pier. Outfitters in town simplify logistics—shuttles for larger boat tours, hourly rentals for kayaks and bikes, and curated city and bus tours that place Highwood in the wider Lake County context. For itinerary-minded travelers this means stacking experiences (sailing + walking tour + photography) without long transfers, while families and casual explorers appreciate the short, manageable outings and the friendly, well-informed local guides. Whether you’re a first-time kayaker, an angler seeking local tips, or someone who simply wants a short escape from the city with good food and great light, Highwood offers a compact, inviting palette of outdoor experiences.

Highwood’s geography makes it a natural hub for mixed-activity days. Start with a morning boat tour to read the lake’s mood, then switch to a city tour or walking tour that unpacks local history and architecture. Afternoon kayak sessions and boat rentals give you control of your pace; evenings are for photography walks as light softens over the water.

Local outfitters and guides cater to a range of skill levels. Pick a guided sailing or fishing trip for a low-fuss introduction to the lake, or rent a bike for a self-led excursion that connects parks, piers, and cafes. Winter activities and off-season programming are smaller-scale but rich with quiet parks and lake vistas.

Choose Your Adventure Level