3 Incredible Early Autumn Getaways

Sep 21, 2025

Today we’re celebrating the first day of fall in style! We’re bringing you three incredible destinations for an autumnal getaway to ring in the season. Whether you’re looking for classic leaf-peeping and fall photography backdrops or you’re interested in some seasonal fishing or looking to take a hike through the changing foliage, you’ll find the perfect place to visit on our list. We’re heading to the Northwoods in Wisconsin, the village of Hermann in Missouri, and the Keweenaw Peninsula in Michigan. We’ve also made sure to include several options for scenic drives or walking tours at each destination so you don’t miss a minute of that fine foliage.

So, what are you waiting for? Hop in your new car from Classic Toyota of Waukegan and let’s hit the road to adventure.

Northwoods: Wisconsin

RR60 (Rustic Route 60) is more than 11 miles of paved road that winds through the stunning Northern Highland/American Legion State Forest. This beautiful road trip is a worthy stretch of road winds through coniferous and hardwood forests and past old logging camp sites, stunning hiking trails, and an old saw mill near Star Lake. You’ll want to make sure to drive carefully, as the area is rife with wildlife! Stop off on any of the numerous scenic vistas and check out the beautiful lakes of the Northwoods and capture some gorgeous wildlife photography.

The Bayfield Peninsula and Apostle Islands Area is a top notch opportunity to experience the magic of the Northern Lights and an autumnal campout!

Boulder Junction has nearly 200 lakes to choose from for an afternoon of fishing, boating, kayaking, and paddleboarding. The fish are plentiful here including musky, northern pike, smallmouth bass, walleye, bluegill, perch, and crappie. There are numerous paved and unpaved trails for mountain biking and hiking through the gorgeous autumnal forests.

Manitowish Waters offers exquisite autumn foliage viewing from mid-September to late October depending on weather conditions. It’s also the perfect place to take a tour of a local cranberry marsh and learn about this traditional seasonal harvest at Manitowish Waters Cranberry Marsh Tours. (For even more cranberry fun, check out The Cranberry Highway, a 50 mile stretch of road that passes through several marshes including Wisconsin Rapids, Pittsville, Nekoosa, and Tomah.)

Eagle River’s Chain of Lakes offers an incredible opportunity to take in the foliage on different lake waters while paddling, boating, and fishing. Not to mention the wonderful hiking trails that weave you through maple, oak, and birch trees as they change a plethora of sunset hues.

Hermann, Missouri

This picturesque village offers a lively annual Oktoberfest to honor the region’s rich German cultural heritage. Enjoy craft beer, local wine and spirits, authentic German food, German folk music and dance demonstrations, and much more!

The Hermann Wine Trail is a group of 6 family-owned wineries in the region: Adam Puchta Winery, Dierberg Star Lane, G. Husmann Wine Company, Hermannhof Winery, Reserve Cellars of Hermann, Robller Vineyard. Purchase your tickets in advance (21+!) and pick up a souvenir glass at your first stop, and enjoy stunning views of the area at each unique vineyard and wine-tasting room.

Take a walking tour of the local area’s German Heritage and history with Bayer Walking Tours, City Park Walking Tours, the Historic Buildings of East 2nd Street Walking Tour, and Riverfront Walking Tour.

The Grand Bluffs Conservation Area is 236 acres with a beautiful stretch of dolomite bluffs overlooking the Missouri River, with unmatched views of the changing autumnal foliage!

Keweenaw Peninsula, Michigan

Autumnal foliage in this area is at its peak in the last week of September and 1st two weeks of October, so now is the perfect time to visit! If you’re lucky, some of the areas a little further south such as Copper Harbor and Isle Royale may peak a little later to extend the season further.

Take a spectacular scenic drive on the Brockway Mountain DRive between Eagle Harbor and Copper Harbor that winds up the top of Brockway Mountain. On the clearest day you’ll see for miles and enjoy one of the best views in the Upper Peninsula!

Keweenaw’s International Dark sky Park has incredibly low light pollution and unmatched night sky viewing for the Northern Lights and shooting stars!

Pike Bay is an excellent autumnal fishing and paddling spot. Anglers will be thrilled to find plentiful fish, and you’ll catch some great northern pike, crappie, and bluegill here!

The Chassell Historic Trail is one part nature trail and one part history stroll as you learn about the area’s lumber history! Two different lumber companies operated on this land, and a special easement was provided to create a half mile loop through the wetlands. You’ll trek past the Chassell House site and towards the water where the historic mill once operated; there are 9 different signs along the trail to illustrate the history of the logging industry.

The Sturgeon River Slough Wildlife Area and Refuge is a must see nature spot in the region. You’ll head over to the observation tower and look out over the land to look for seasonal migrating birds, deer, black bear, muskrats, osprey, sandhill cranes, and more