Fall Retreats in the Midwest

Woman picking out apples from a bin

Reconnect with nature on a fall trip to an artsy lakeside town, a scenic wine trail, hidden waterfalls, or the rolling hills of the prairie.

Wisconsin, Door County

Shop Local

A creative hub for Midwestern artists, the charming lakeside towns in Door County are filled with local art galleries and shops. Browse Sturgeon Bay’s stores on Third Avenue and pop into Popelka Trenchard Glass to see glass sculptures and demonstrations. Continuing up the peninsula, stop by Edgewood Orchard Galleries’ outdoor sculpture garden and shop for unique creations by regional artists at Clay Bay Pottery in Ellison Bay. Don’t forget to grab a cone at the century-old ice cream parlor, Wilson’s, or take a picture of the famous goats grazing on the sod roof of Al Johnson’s Swedish Restaurant.

Fall Festivities

This Lake Michigan destination boasts fall festivals almost every weekend in September and October. Visit dairy cows and wander the giant corn maze at the Dairy View Country Store. Pick your own apples at Lautenbach’s Orchard Country Winery & Market, gobble up seasonal pastries at Seaquist’s Farm Market, and sip hard ciders at Island Orchard Cider.

See the Colors

View foliage on a hike through Potawatomi State Park in Sturgeon Bay or climb up the tallest sand dune, Old Baldy, in Whitefish Dunes State Park to see the colors from above. Kayak out to Cave Point to see jagged limestone bluffs or bike to Schoolhouse Beach’s pebble-covered shore on Washington Island.

Man walks across the Pomona Natural Bridge in Illinois
Pomona Natural Bridge

Photo by Illinois Office of Tourism

Illinois, Shawnee Hills

Sip and Savor

With 11 wineries nestled into the Shawnee National Forest in southern Illinois, the Shawnee Hills Wine Trail offers a great multi-day wine experience in nature. Most of the vineyards are located in clusters, so it’s easy to visit three to four wineries per day. Some highlights: freshly baked bread and olive oil paired with award-winning wine at the Tuscan-inspired Blue Sky Vineyard, Swedish-influenced wine and food at Hedman Vineyards, fruit wines at Pomona Winery, and the fall-favorite Hot Honker Hill Hooch at Honker Hill Winery.

Take a Detour

Explore the Little Grand Canyon for mesmerizing views of the Mississippi River bluffs. Scamper across the Pomona Natural Bridge—a 90-foot-long sandstone bridge created by water erosion in the Shawnee National Forest—and examine towering rock formations in Giant City State Park. For an exciting group outing, try a zip-lining excursion through the trees on a Shawnee Bluffs Canopy Tour.

Rest Easy

Wake up to vineyard views by staying in a suite at Blue Sky Vineyard, Hedman Vineyards, Kite Hill Vineyards, or Von Jakob Vineyards on the Shawnee Hills Wine Trail. An abundance of cabins and B&Bs in the area include the hobbit-style cottages at Rocky Comfort Cabins and the five-bedroom farmhouse on a private lake at Wine Country Farmhouse.

Fall trees and a pond in the Porcupine Mountains in Michigan

Michigan, Porcupine Mountains

Hunting for Waterfalls

The Porcupine Mountains offer a good waterfall scavenger hunt alternative to Minnesota’s familiar North Shore. There are more than 150 waterfalls in the western Upper Peninsula, and several within Porcupine Mountains Wilderness State Park. Two falls-filled routes include a stretch along the Little Carp River and Presque Isle River on the state park’s western edge. Less than an hour’s drive from the park are two of the most picturesque waterfalls in the region. Agate Falls features a series of falls over a sandstone shelf nearly 40 feet high, while Bond Falls has a roaring 50-foot drop.

Climb to the Tallest Peak

Panoramic views of the fall-colored forest await atop the Summit Peak Observation Tower, the highest point in the Porcupine Mountains at close to 2,000 feet above sea level. To see one of the most photogenic areas of the park, hike along either the Escarpment Trail or the Big Carp River Trail to discover the Lake of the Clouds valley surrounded by an old-growth forest. For another spectacular overlook, ride the chairlift to the top of the Porcupine Mountains Ski Area to see bursts of color and the deep blue of Lake Superior.

Explore the Visitors Center

Learn more about the wildlife and mining history of the 60,000-acre park at the Porcupine Mountains Visitor Center. Sign up for a guided hike with a park ranger to see some of the park’s best sites, including hiking to Summit Peak at sunset, exploring a bear den, and watching the night sky at the Lake of the Clouds observation area. The visitor center also provides accommodation information on lodge suites, cabins, yurts, and campsites.

Family dressed in German garb at the Amana Colonies Oktoberfest celebration in Iowa
Millstream Brewing Company’s Oktoberfest

Courtesy Amana Colonies CVB

Iowa, Amana Colonies

Walk Back in Time

Appreciate a more simple, grounded way of life by visiting the idyllic seven villages of the Amana Colonies, founded by German settlers in 1855. Today, the colonies are a thriving attraction in Iowa. Book a tour with the Amana Heritage Society to see the communal kitchen, the Amana Community Church Museum, the blacksmith shop, the High Amana General Store, and more. Shop at the Amana Woolen Mill and antique stores for quality handcrafted goods such as wool blankets, rugs, furniture, grandfather clocks, pottery, and wooden toys.

Tasty Traditions

Dig into German staples like schnitzel, strudel, and sausages made from recipes passed down from the original settlers at Hahn’s Hearth Oven Bakery, the Amana Meat Shop and Smokehouse, and local restaurants. Sample specialty fruit wines at Ackerman Winery and beer at Iowa’s oldest brewery, Millstream Brewing Company. For the true German experience, visit October 4-6 for the annual Oktoberfest, complete with a beer garden, games, a parade, and more.

Life on the Prairie

Experience the Amana way of life by taking art and quilting classes at the Amana Arts Guild or watching a performance at the Old Creamery Theatre Company. Explore the fall landscape on a bike ride around Lily Pond and sleep soundly after a day of adventures at one of Amana’s many B&Bs and inns.

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