Small-town Wisconsin trips, big time summer fun

If small-town quality time is on your summer bucket list, look no further than Wisconsin. Here are three of our picks for getting away from it all — way closer than you’d think. 

Washington Island, WI

A year-‘round island five miles off the tip of Door County, Washington Island is the largest of the thirty, with a whopping 35 square miles to explore. It’s a bit more of a hike from Chicago (about 300 miles, including a short ferry ride). Bring your car on the ferry to get around the 100 miles of paved roads on the island — but be prepared to want to bike or stroll around this spot that seems worlds away from the everyday. 

Places to stay: The historic Hotel Washington offers up oodles of old-time charm — but boasts modern takes, too. (Yoga or art workshops in the Studio, anyone?) Cottage rentals abound in this postcard of an island, too, most with water access or views.

Where to eat: Want to earn some cred with the locals? Take a shot and join the Bitters Club at Nelsen’s Hall Bitters Pub & Restaurant, the oldest pre-Prohibition tavern in Wisconsin — due to the high-proof Angostura bitters being allowed as a “health tonic.” (This family-friendly pub is also rumored to be haunted by the ghost of Nelsen himself!) Red Cup Coffee House is everything you’d want in a small-town coffee shop (including organic goodies and a bevy of sweet gifts), and locals love Island Pizza for its proximity to the ferry — and did we mention that the pizza is hand-tossed?

Things to do: One of only five similar sand-less beaches in the world, Schoolhouse Beach is a must-see. Crystal waters and glacier-polished limestone pebbles ensure photos ops like no other, but remember: there’s a hefty fine for taking any of these protected “treasures” home! Visiting in July or August? Fragrant Isle — the Midwest’s largest single site grower of lavender — will be in full bloom, and taking a tour of the fields will ensure sweet sleep for the entirety of your island visit. And if you feel like taking a short jaunt, a 20-minute ferry will get you to Rock Island, Wisconsin’s only state park that’s an island. An impressive lighthouse, Potawatomi, was the first one commissioned in these waters, but there’s no wrong way to explore this island. (It also houses a sandy beach that’s considered one of the nicest in Door County.)

Oconomowoc, WI

With a population of around 16,000, the quiet lake town of Oconomowoc has the utterly fitting tagline of “life comes naturally here.” Featuring turn-of-the-century homes on leafy streets leading to a picturesque (and walkable) thoroughfare, there’s no shortage of charm here. Looking for a bit of Americana on a quick weekend getaway, a mere 120 miles from Chicago? This is the place.

Places to stay: The Inn at Pine Terrace is a stunning bed & breakfast as well as a historic mansion. Experience the grandeur of the parlor, turrets and thoughtfully appointed details — but definitely make time for a swim in their outdoor pool. The Staybridge Suites are a great option for families, especially with the 9-seat movie theater, indoor pool, hot breakfast buffet and, most importantly, easy access to the town’s many swimmable lakes and beachfronts. 

Where to eat: Once a bustling train depot with 65 trains a day passing through, Maxim’s at Oconomowoc Depot is a must for families looking for great dining options — as well for rail fans jonesing for some depot artifacts. Open only during the summer season, the Kiltie Drive-In is a throwback to a much cooler era. Come for the car hop service, stay for the custards and malts, onion rings and Kiltie Burgers (more Sloppy Joe than burger, and worthy of a fistful of napkins). 

Things to do: Fox Lake Country Antique Mall is a treasure-hunters paradise, and the 100+ vendors ensure you’ll be able to add to your collection of … whatever it is you love to collect. (They have an exceptional array of vintage toys and games, too!) The Rhodee Memorial Band Shell is the place to be every week during the summer, especially for the Wednesday Oconomowoc American Legion Band concerts, as well as the Friday night Bands at the Beach. Located on the shore of Lac La Belle at City Beach, there are few nicer spots to while away a summer evening. 

Spring Green, WI

When artists take up residency in River Valley’s tiny Spring Green (pop: 1,652), magical things happen. The summer home of globe-trotting actors, this spot (about 200 miles from Chicago) also hosts architectural wonders — as well as more than a few spots to really catch your breath. 

Places to stay: The House on the Rock Resort is an unapologetic throwback in terms of decor but, with its great pool, pristine golf course and surrounding wooded areas, it’s an exceptional place to unwind. (Each room has its own terrace, too.) The House on the Rock Inn is a lower-key option, but on the plus side for kiddos? The play pool features a 45-foot long submarine. 

Where to eat: Freddy Valentine’s Public House, now a gastropub-meets-sports bar, was an imposing bank building in a former life. (Try to snag a table in the Vault Room.) Wisconsin knows its drive-ins, and Rumble Seats is certainly a fun one. A playground adjacent to the restaurant (eat-in and carhop services are available) will thrill the smaller set — and the abundance of Marilyn and Elvis ephemera will thrill the ‘50s-lover. 

Things to do: Founded in 1977, American Players Theatre has been home to world-class theater (and theater artists) ever since. Join the enthralled crowds on a lantern-lit path to the beautiful amphitheater, or take advantage of the modern amenities of the smaller Touchstone Theatre. Looking for something a little out of the ordinary? Alex Jordan’s mind-blowing creation, the House on the Rock Attraction, almost defies explanation — not to mention gravity. Started in 1945 on Deer Shelter Rock, this manor of curiosities cannot be fully experienced a day. (But you’ll sure have fun trying!)

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