Fish Creek, Wisconsin

Drive time from Chicago: 4.5 hours

Follow local talent north to American Folklore Theatre (folkloretheatre.com) in Peninsula State Park. On June 11 it debuts Strings Attached, a new musical by Chicago-based Dave Hudson that tells the tale of twins separated at birth: One plays the ukulele, the other the banjo. Wacky meets country in Seaquist Segway (seaquistsegway.com), featuring off-road tours through orchards and forests on Segways fitted with ATV tires. Grab trail snacks, cherries, and preserves at the unrelated Seaquist Orchards Farm Market (920-854-4199). While the newly expanded Ridges Sanctuary (ridgessanctuary.org), the state’s oldest nature preserve, breaks ground on a nature center this summer, visitors can hike its ridges and swales in search of native orchids. Last summer, the Skyway Drive-In Theatre (doorcountydrivein.com) invested in digital projection and with it a promising future in retro cuddling. Rent one of the six bayside antique-filled cottages run by Thorp House Inn & Cottages (thorphouseinn.com; cottages from $155) to temporarily make like a townie.

Two Rivers, Wisconsin

Drive time from Chicago: 3 hours

Once upon a precomputer time, Hamilton Wood Type was the world’s biggest distributor of wood blocks for printing presses, a legacy preserved by the Hamilton Wood Type & Printing Museum (woodtype.org). It’s a rambling, cavernous collection of antique saws and shapers, early printing presses, and rotating exhibits of graphic design. The lakefront museum houses a gift shop with cool stationery for those who appreciate but can’t replicate. Design fans can indulge in the Bernard Schwartz House (theschwartzhouse.com; from $350 per day), a 1940 Frank Lloyd Wright Usonian four-bedroom home available for rent.

Sheboygan, Wisconsin

Drive time from Chicago: 2.5 hours

The Kohler family largesse makes Sheboygan a destination not just for the company’s resorts and golf courses but also for its John Michael Kohler Arts Center (jmkac.org). Arts/Industry, through August 31, exhibits 350 large-scale works by artists who used Kohler’s pottery, foundry, and enamel shops to make things on a scale impossible in a studio. Hike the dunes at lakeside Kohler-Andrae State Park (dnr.wi.gov), then go for one of the new thermal treatments at Kohler Waters Spa, a key attraction of the American Club (americanclubresort.com; rooms from $346) in nearby Kohler. Taste the first vintages at just-opened Blind Horse Restaurant & Winery (theblindhorse.com), inside a 130-year-old farmhouse.

Cedarburg, Wisconsin

Drive time from Chicago: 2 hours

The former mill town continues to stuff shops and attractions into its handsome 19th-century limestone buildings, including the new Chiselled Grape Winery (chiselledgrape.com), noted for its dry whites and rich ports. Opened in late 2013, the Cedarburg Art Museum (cedarburgartmuseum.com) exhibits a rotating selection of its Wisconsin- and nature-themed collection and often showcases works from the annual Cedarburg Plein Air Art Event (cedarburgpleinair.com), which runs this year from June 18 to 29. After you’ve filled up on art, chill out with a shredded tenderloin sandwich and a Lake Louise Kiss the Lips IPA, among 30 beers on tap at the new gastropub the Stilt House (stilthousegastrobar.com).

Milwaukee

Drive time from Chicago: 1.5 hours

Shut out of Lolla? Lady Gaga, the reunited Outkast, Joan Jett, and Neon Trees will headline Summerfest (summerfest.com), from June 25 to July 6. Hop across the Milwaukee River to emerging Walker’s Point, home to warehouse-size antique malls and hits of the city’s dining scene. Sample flavors such as Brandy Old Fashioned at Purple Door Ice Cream (purpledooricecream.com) and queue up for Gruyère cheeseburgers and octopus panzanella at All Purpose (apbarandkitchen.com). Browse vintage 45s, cowboy boots, and sofas at the new pop-up flea market One Trick Pony (onetrickponymke.wordpress.com), held periodically at Anodyne Coffee Roasting Company (anodynecoffee.com). Just west of downtown, catch $3 tap PBRs and games of cornhole on the patio at Jackson’s Blue Ribbon Pub, the new tavern in the old Pabst brewery. The long-shuttered Pabst complex has been adapted as the Brewhouse Inn & Suites (brewhousesuites.com; rooms from $189).

Traverse City, Michigan

Drive time from Chicago: 5 hours

Flanked by wineries on nearby Old Mission and Leelanau Peninsulas, this northern hub has carved a quaffable niche in beer, with 13 microbreweries and brewpubs. The latest is Rare Bird Brewpub (rarebirdbrewpub.com), crafting a dozen or so options—including a cream ale billed as the perfect post- lawn-mowing refresher—in a former cannery. The year-old Brewery Terra Firma (breweryterrafirma.com) aims to be the city’s first farm-to-stein brewer, harvesting hops, herbs, and honey from its own farm. The Workshop Brewing Company (traversecityworkshop.com) serves seven standard “journeyman” beer varieties along with “one-hander” sandwiches that won’t separate you from your pint. Work up to your beer crawl by renting a kayak from the River (therivertraversecity.com) in newly renovated Clinch Park downtown. Explore the arty side across the street in the new Bijou by the Bay cinema, home to the Traverse City Film Festival (traversecityfilmfest.org) from July 29 through August 3, or take to the water aboard Scout, a six-passenger, 38-foot cutter, just launched by Traverse Tall Ship Company (tallshipsailing.com). Stay and catch the sunrise from waterfront Bayshore Resort (bayshore-resort.com; rooms from $133).

Muskegon, Michigan

Drive time from Chicago: 3 hours

Families flock here for Michigan’s Adventure (miadventure.com), a roller-coaster theme park, and the 26 miles of surrounding beaches. But the city’s once-downtrodden downtown is making a comeback. Stock your picnic hamper on Tuesdays, Thursdays, and Saturdays at the new Muskegon Farmers Market (muskegonfarmersmarket.com), featuring produce stands and baker stalls, or sift through the neighboring trash-to-treasure flea market on Wednesdays. Part of Michigan’s brew boom, Pigeon Hill Brewing Company (pigeonhillbrew.com), with its vintage photos and tables fashioned of lake-salvaged wood, is one of two microbreweries recently opened. Unruly Brewing Co. (unrulybrewing.com) taps highly hopped IPAs and other rotating drafts made by former homebrewer Eric Hoffman. Dine at the farm-to-table restaurant Mia & Grace (miaandgrace.com) before hitting the sack at the waterfront Shoreline Inn (shorelineinn.com; rooms from $99), which overlooks Muskegon Lake.

Saugatuck, Michigan

Drive time from Chicago: 2 hours

Western Michigan’s hippest town was overdue for a standup paddleboard rental shop before Shaka Surf (shakasurftours.com) opened last summer, offering lessons and tours on the generally calm harbor. Towel off to tipple flights featuring Michigan vintages amid global favorites at Petter Wine Gallery (petterwinegallery.com), a new offshoot of neighboring Button-Petter Gallery. The two-year-old Saugatuck Motel (thesaugatuck.com; rooms from $89), one of the beach town’s string of mod motel conversions, replaces the old Shangrai-La, keeping the 1960s kidney-shaped pool and updating its 20 rooms with painted pine-panel walls and modern bathrooms. When you leave town, detour 10 miles southwest to Fennville to sample Virtue Cider (virtuecider.com), surrounded by apple orchards.

Sawyer, Michigan

Drive time from Chicago: 1.5 hours

Move over Redamak’s. Harbor Country newcomer State Fare and Provisions (269-409-3595) does diner fare with respect for ingredient provenance, producing skin-on fries and meaty two-fister burgers. From its base in New Buffalo, Third Coast Surf Shop (thirdcoastsurfshop.com) serves thrill seekers the latest in sliding sports: sandboarding—think snowboarding, but on dunes. The outfitter guides private sandboarding lessons at Warren Dunes State Park (michigan.gov/dnr) and also delivers standup paddleboards to the beach so you don’t have to schlep. Rabbit Run Inn (rabbitruninn.com; rooms from $190) rounds out your recreational needs with loaner bikes, beach chairs, and umbrellas.

Porter, Indiana

Drive time from Chicago: 45 minutes

Climb 176-foot Mount Jackson, 184-foot Mount Holden, and 192-foot Mount Tom at Indiana Dunes State Park (indianadunes.com) this summer to conquer the 3 Dune Challenge (3dunechallenge.com) for free bumper stickers and more valuable bragging rights. The 1.5-mile route—distance not including backsliding in the sand—angles up to 40 degrees. The park’s new 100-acre offshore J.D. Marshall Preserve (in.gov/dnr/) protects the wreckage of a 1911 hauler that was carrying 1,000 tons of sand when it capsized in a storm; scuba dive with Windy City Diving (windycitydiving.net) to see it. Refuel with a wood-fired pizza issued from a vintage 1949 Studebaker repurposed as Rolling Stonebaker (rollingstonebaker.com), parked near the Beverly Shores train station through October.