Top 15 Things To Do in Highwood, Illinois

Highwood's compact downtown sits a short push from the North Shore's lakefront and slips into a seasonal rhythm keyed to watercraft: early-morning anglers casting from quiet harbors, families piloting pontoons for a slow afternoon, and sunset runs with the Chicago skyline a faint promise on the horizon. This guide focuses on renting boats around Highwood—what to expect from the water, how to choose the craft that fits your plans, seasonal considerations, and smart packing for a day afloat.

Compact, charismatic, and unexpectedly textured, Highwood condenses small-town storefront charm, a lively culinary scene, and immediate access to lakefront and forest preserves into strollable sightseeing loops. This guide focuses on curated walking, culinary, and short-drive tours that reveal why locals prize this pocket of Lake County.

Highwood sits like a small, beached watchtower on the North Shore—compact, rooted in lake culture and a practical jumping-off point for sailors who prize quick access to Lake Michigan’s broad water and fickle moods. This guide focuses on sailing opportunities accessible from Highwood and the surrounding North Shore corridor: short day sails, race days, learn-to-sail programs, and the kind of afternoon cruises that fold a city skyline into a distant, luminous horizon.

Compact, culturally vivid, and built along a bluff that looks out over Lake Michigan, Highwood is a walking-town in miniature — where a 90‑minute stroll can fold in architecture, immigrant history, intimate galleries, and shoreline views. This guide focuses on walking tours: self-guided neighborhood rambles, themed culinary routes, and guided history walks that reveal why this small North Shore city punches well above its weight for pedestrian exploration.

Highwood is a compact, shoreline-facing gateway for paddlers who want quick access to Lake Michigan’s open water and sheltered urban lagoons. Expect short launches into wind-swept blue expanses, calm estuary pockets alive with birds, and easy connections to neighboring launches for half-day traverses. This guide focuses on kayaking in and around Highwood — what to expect on the water, how to plan around weather and traffic, and complementary activities once you’re off the water.

A compact North Shore enclave with instant access to Lake Michigan and a web of nearby inland waters, Highwood is an underrated launch point for anglers. From early-morning surf casting off rocky stretches to easy pier fishing and short drives to productive inland ponds, the area offers accessible freshwater opportunities framed by small-town character and big-lake drama.

Compact, character-filled, and perched a few blocks from Lake Michigan, Highwood makes an unexpected hub for curated bus tours that fold local history, shoreline scenery, and food-and-drink culture into relaxed, accessible day trips. Whether you want a short shuttle to a nearby nature preserve, a guided history loop through fortified neighborhoods, or a craft-beer crawl that keeps all the logistics off your plate, Highwood’s small-town streets and proximity to the North Shore create bus routes that are scenic, low-stress, and rich with local color.

Highwood is a compact, walkable North Shore town that punches above its weight for bike rentals. A short Metra ride from Chicago and framed by lake-scented breezes, its rental shops serve casual cruisers, e-bike explorers, and roadies looking to stitch together scenic point-to-point rides. This guide focuses specifically on renting bikes in Highwood: the terrain you’ll ride, seasonal considerations, how rentals integrate with public transit, and practical tips for choosing the right two-wheeled companion for your day along the shore and into nearby preserves.

Highwood is a compact, lively starting point for short bike tours that stitch together lakefront vistas, tree-lined residential streets, and the quieter greenways of northern Lake County. Expect a mixture of calm neighborhood lanes, short coastal stretches, and nearby forest-preserve connectors that make this an ideal base for curated half-day and full-day rides—whether you’re rolling a hybrid, an e-bike, or a gravel rig.

Tucked into the North Shore a short drive from Chicago, Highwood compresses a surprising number of photogenic scenes into a walkable, intimate town: weathered brick storefronts, a compact cultural district, shoreline bluffs and the architectural bones of Fort Sheridan. Photography tours here reward curiosity — early-morning light on the lake, festival-lit streets in summer, and migrating songbirds in spring all provide distinct subject matter across short distances. This guide focuses on how to plan a photography-focused visit to Highwood: where to shoot, when to go, what to pack, and how to combine complementary activities like birding, architectural walks, and off-season long-exposure shoreline sessions.

Highwood’s zoo and small-animal offerings are less about headline attractions and more about intimate encounters: hands-on learning at community farms, close-up raptor demonstrations, and neighborhood wildlife sanctuaries where the pace is calm and the access is personal. This guide focuses on how to make the most of those experiences—seasonal rhythms, practical planning, and how to pair a visit with nearby outdoor activities like shorebird watching and preserve walks.

Highwood’s winter is less about alpine peaks and more about a practiced, local seasonal rhythm: short, crisp days, neighborhood sled hills, frozen pond silhouettes and forest-preserve loops trimmed in ice. This guide focuses on winter-specific outdoor pursuits around Highwood—skating and neighborhood sledding, cross-country skiing and snowshoeing in nearby preserves, winter birding along the lakeshore, and complementary indoor and cultural options that keep a cold-day itinerary balanced and lively.