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4 Great Road Trips for Memorial Day Weekend

Here are four favorite Midwestern destinations, each less than a five-hour drive from Chicago.

Blue Sky Vineyard, a member of the Shawnee Hills Wine Trail.   Photo: Courtesy of Blue Sky Vineyard

Elevate your Memorial Day weekend plans with a road trip to a hopping Midwestern destination. Here are four favorites, each less than a five-hour drive from Chicago.

1. Lake Geneva, Wisconsin

DRIVE TIME: 1.5 hours
WHY GO: Four beaches, watercraft rentals from kayaks to speedboats, and the beautiful historic cruises—including unique U.S. mail delivery boat tours—of the Lake Geneva Cruise Line make Lake Geneva all about fun on the water. For another diversion, drive 20 minutes to the Burlington ChocolateFest (May 22 to May 25) for a chef showdown, boat races, and military exhibits.
STAY: Get a drink in the speakeasy and lay your head where General Grant once did at the 19-room Maxwell Mansion 1856, which revealed its new mod-meets-throwback Carriage House rooms in December (from $185). Golfers should stay at the sprawling, 335-room Grand Geneva for a special rate at the Brute and Highlands courses of ($89 for the first round of golf, $39 for the second; rooms from $199).

2. Madison, Wisconsin

DRIVE TIME: 2.5 hours
WHY GO: Pure Americana comes in the form of Madison’s four-day Brat Fest, with Bret Michaels and the Charlie Daniels Band among the headlining musical acts that will span three stages. Check out the carnival, sign up for the 10K Bun Run, catch the UW Marching Band parade, and see fireworks on Sunday. On Saturday, go to the Capital Square for the Dane County Farmers’ Market, the largest producer-only farmers market in the country. On Sunday, runners can take off from Capital Square and the start line of the Madison Half Marathon ($85 entry fee).
STAY: On Wednesday, Chicago-based AJ Capital Partners opens the playful 72-room Graduate Madison, the third from the new college-town-inspired Graduate Hotels collection. AJ Capital’s portfolio includes Chicago’s Hotel Lincoln, Soho House Chicago, and the forthcoming Chicago Athletic Association.

3. Indianapolis

DRIVE TIME: 3 hours
WHY GO: Watch Ed Carpenter vie for pole position for the third consecutive year in a row at the Indy 500, happening at the Indianapolis Motor Speedway on Sunday, May 24. Enjoy the festivities leading up to the epic race: On Friday, see a vintage car exhibition, the Indy Lights rookie race, and an O.A.R. and Jane’s Addiction concert ($40); on Saturday, check out the 500 Festival Parade in downtown Indy, Florida Georgia Line concert ($40), and Snakepit Ball ($275).
STAY: Most of Indy’s hotels are sold out by now, so why not give Airbnb a try? One search revealed a downtown penthouse that sleeps six for $300 a night.

4. The Shawnee Hills Wine Trail

DRIVE TIME: 5 hours
WHY GO: Two Illinois–produced wines—a cabernet franc and a brut—are among the vintages served at Alpana Singh’s new Seven Lions. Discover more of the state’s vino with a trip south to the 40-mile Shawnee Hills Wine Trail, a certified American Viticultural Area in southern Illinois made up of 12 wineries. At the family-owned Alto Vineyards, try the chillable Heartland Red and the sweet Porto di Guido. Go for the Tuscan scenery at Blue Sky Vineyard, where you should sit back on the outdoor terrace with a glass of Chambourcin, a regional full-bodied favorite. In between tastings, take some time for a hike at Giant City State Park.
STAY: Fifteen minutes from the nearest winery (StarView Vineyards), stay in Anna, Illinois, at the 11-suite Davie School Inn, a 1910-built public school reopened in 2004 as an historic boutique hotel (from $100).

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