3 Fall Weekend Luxury Getaways in the Midwest

From the shores of Lake Michigan to the north woods of Wisconsin, the Midwest is known for its scenery and beauty, and there’s no better time to embrace that beauty than right now. Here are three luxury fall weekend getaways in the Midwest, where you can enjoy the outdoors and get some rest and relaxation in lavish comfort.

Wisconsin: Hike the Ice Age Trail and Enjoy MKE

More than 1,000 miles of glacial scraped land left behind scenic water-filled kettles, hilly moraines and other formations that makeup the Ice Age National Scenic Trail in Wisconsin.

The Ice Age Trail Alliance offers plenty of day hikes throughout the state from Milwaukee to Madison or farther north near the Minnesota border. More than 45 miles are located in various Milwaukee suburbs of Waukesha County.

For an easy route, try the 3.1-mile Monches segment of the Ice Age Trail in Hartland, Wisconsin, just west of the Milwaukee metro area. Meander the peaceful wooded trail that runs alongside the Oconomowoc River. Walk through a mature maple forest on wood-plank bridges over the flowing river and rock-filled streams for a great display of fall foliage.

Stop for wine and charcuterie at Tabi’s Lake Country. With more than 800 choices of vino, there’s a wide selection.

Luxury Fix: Stay in downtown Milwaukee at The Pfister Hotel. Built in 1893, this four-star hotel offers modern amenities with the opulence of the Gilded Age. Wander the expansive Victorian art collection—the largest of its kind in any hotel in the world. Grab a martini, listen to live music and enjoy incredible panoramic downtown views at Blu, the cocktail lounge on the hotel’s 23rd floor. Visit the spa for a Rhassoul Mud body treatment that’s done with Moroccan-imported mineral clay.

Eat at James Beard award-nominated Lupi & Iris. The sleek spot offers a prix fixe menu with seasonal ingredients inspired by the French and Italian Riviera. Shop boutiques and visit art galleries in the Historic Third Ward. For a taste of Octoberfest, check out Lakefront Brewery, known for its raucous brewery tours, fish fries, sausage flights and expansive line-up of beers including a few gluten-free offerings.

Indiana: Visit Covered Bridges and Indy

With 31 historic covered bridges, Parke County, Indiana is known for having the largest concentration of covered bridges in the world. Parke County is located about an hour and half west of Indianapolis or three and a half hours from downtown Chicago.

Every October, there’s a 10-day Covered Bridge Festival that starts on the second Friday of the month. The covered bridges are spread among ten small towns: Rockville, Bellmore, Billie Creek Village, Mansfield, Bloomingdale, Bridgeton, Rosdeal, Mecca, Montezuma and Tangier.

Back in the horse-and-buggy days of the 1800s, these were known as “kissing bridges” for courting couples, who were momentarily out of view along the road. The Bridgeton Covered Bridge, which includes a dam and mill, is considered the most famous. In Rockville, visit the Amish-run, cash-only Bellmore Country Store.

Luxury fix: Stay in Indianapolis at the JW Marriott close to White River State Park. Visit the underrated Eiteljorg Museum known for its native and western art. Dine at Vida with its contemporary four-course tasting menu or the Livery, a Latin-inspired restaurant that’s housed in a refurbished horse stable.

For a German-inspired Octoberfest, visit The Rathskeller, an infamous Bavarian-style beer hall or grab a cocktail at 1933 Lounge by St. Elmo, a swanky speakeasy located above the landmark St. Elmo Steak House. Looking for more? Go to Massachusetts Avenue aka Mass Ave, with its eclectic boutiques, and check out the nightlife in Broad Ripple.

Michigan: Drive the M-22 Scenic Fall Color Route

Highway M-22 hugs Lake Michigan’s shoreline beginning in Manistee, Michigan and heading north to Traverse City in the northwest corner of Michigan’s Lower Peninsula. Drive 116 miles through breathtaking scenery, past vineyards, orchards and small picturesque towns.

Stop at Point Betsie, which many say is Michigan’s most photographed lighthouse and grab a Belgian-style ale at Stormcloud Brewing in Manistee. Check out the Empire Bluff Trail’s Scenic Lookout in Leelanau County, and visit Sleeping Bear Dunes National Lakeshore, known for its 450-foot bluffs and sandy beaches.

Explore the Leelanau Peninsula Wine Trail, which includes over 20 wineries in the towns of Leland, Northport, Suttons Bay and Glen Arbor. Book a VIP Tour through Scenic Wine & Brew Tours. The 5-hour tour includes a chauffeured ride in a GMC Yukon Denali and features stops at 4 to 6 wineries with door-to-door service and reservations. “All you have to do is get into a vehicle and enjoy the location,” says owner Dan Penning.

Stop at Leland’s historic Fishtown district. It’s one of the last working fishing districts on the Great Lakes and the oldest and largest Ottawa village. Grab a pretzel bread sandwich at Village Cheese Shanty or buy smoked Lake Michigan white fish from Carlson’s Fishery.

Luxury fix: Enjoy seasonally inspired fine dining at The Riverside Inn in Leland. Stay at The Inn at Black Star Farms, a 160-acre winery estate in Suttons Bay that feels like it’s out of a Hallmark movie. Enjoy wine tastings, the horse stables and a chef-prepared breakfast, plus a bottle of wine in your room at check-in.

Or rent a 2,500-square foot private residence at LeBear Luxury Residential Club In Glen Arbor. Each two-bedroom rental includes a private study, two and a half baths, gourmet kitchen and a private deck that overlooks Lake Michigan. Amenities include a fitness center, indoor pool, sauna and massage room.

Written by @properties
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