2025's Towns In Illinois That Come Alive In The Fall
Fall in Illinois brings a somewhat short, but eye-catching season of color, transforming this Midwestern state's river valleys, parks, and historic sites into some of the best travel destinations in the region. From the bluffs of the Mississippi to the wooded hills of the Shawnee National Forest, the various landscapes here shift into reds, oranges, and golds between late September and late October.
Furthermore, a number of small towns across Illinois make the most of the end of the year with harvest festivals and Halloween-themed community events the whole family can enjoy. With that, the following spots this article will discuss highlight where and when to go for the most rewarding experiences this fall.
Ottawa
Ottawa, located at the confluence of the Fox and Illinois Rivers, is a practical base for a getaway for those living in nearby Chicago. Try arriving in early to mid-October, when the surrounding river-formed valleys and nearby parks display colorful foliage all around.
Check out Starved Rock State Park, only a 15-minute drive away, which is arguably the main outdoor attraction in the area for autumn views (and simply an excellent green space any other time throughout the year). The park’s sandstone canyons and high overlooks above the Illinois River make it one of the most photographed fall destinations in the state. Matthiessen State Park and Buffalo Rock State Park, both also nearby, provide some great natural areas, too, along with quieter trails.
In town, Ottawa’s Washington Square offers a central place for afternoon walks among a number of historic structures, with trees changing color around the notable courthouse square. Autumn activities here include the annual Scarecrow Festival in early October, which boasts craft vendors, seasonal foods, and fun family events.
Galena
Galena, in the very far northwest corner of Illinois, is one of the state’s most reliable fall destinations for beautiful sights. The best time to visit is late September through mid-October, when the nearby wooded bluffs along the Mississippi River Valley reach peak color. U.S. Highway 20 provides one of the best approaches into town, offering ideal views of the region's rolling hills, many of which are covered in maples and oaks.
Within town, Grant Park gives a direct vantage point across the Galena River to the old-timey brick buildings lining Main Street. However, for fall foliage beyond the downtown area, Casper Bluff Land & Water Reserve and Horseshoe Mound Preserve are both recommended for their hiking trails and wide overlooks of the surrounding countryside. Moreover, Apple River Canyon State Park, about 30 minutes east, is another worthwhile stop for viewing color in a more secluded setting.
October also brings the Galena Halloween Parade and Festival, one of the largest in the Midwest, featuring floats, costumed participants, and live music. Local orchards and wineries also experience heavy activity in the fall, with tastings and harvest-themed weekends becoming common as the growing season comes to a close.
Woodstock
Woodstock, about 50 miles northwest of Chicago, is also known for its historic square and plethora of fall events. The first half of October is when most of the seasonal action takes place, and when the surrounding McHenry County reaches peak foliage.
The Woodstock Square Historic District, with its 19th-century buildings and central park, is popular mainly for the fact that it is highly walkable, as well as being the main spot to view seasonal color on the tree-lined street alongside farmers' markets and local shops. For broader fall scenes, Moraine Hills State Park and Glacial Park, both within a 25-minute drive, contain networks of hiking and biking trails through wetlands, prairies, and woodlands that turn especially vivid in October. Driving rural backroads around Woodstock also takes you by plots of traditional Midwest farmland framed by beautiful red and gold stands of maples along the way.
As mentioned, Woodstock has a strong fall calendar when it comes to local events. For one, late September draws in thousands of visitors to orchards and cider producers as the region's apples reach their peak, while October brings pumpkin walks and themed events/shows at the iconic Woodstock Opera House. On a side note, this town is also linked to the filming of Groundhog Day, as it was the primary filming location for the classic 1993 film.
Makanda
Makanda is a quaint little community nestled in the Shawnee National Forest. Try arriving in mid to late October, when the forests are colorful but haven't quite shed all of their leaves yet. If travelling by car, the nearby Shawnee Hills Wine Trail is one of the best routes for seeing local woodlands, with convenient overlooks and access points leading to many of the region's unique rock formations and hiking trails. If you're more about getting around on foot, Giant City State Park, just a few miles from town, is especially popular for its bluffs, trails, and panoramic views.
Makanda’s downtown is compact but also fairly active during the autumn season. The Vulture Fest, held in October, is the area’s signature fall event, celebrating the annual migration of turkey vultures with live music, local art, food vendors, and educational zones. Like many other rural spots on this list, a huge variety of nearby orchards and vineyards are open to visitors as well. Feather Hills Vineyard and Winery is just a stone's throw south of town and is completely surrounded by wooded areas that are absolutely gorgeous as the year comes to an end.
Grafton
Grafton, at the meeting point of the Illinois and Mississippi Rivers, is one of the state’s most visited river towns during all seasons of the year, but especially in the fall. The nearby river bluffs are at peak color in October. If that interests you, take a ride down the Great River Road, which runs through town and is recognized as one of Illinois’ premier fall drives. Multiple pull-offs for viewing the changing leaves along the water can be found along the way.
For more outdoor scenery, Pere Marquette State Park, just west of Grafton, is the area's primary destination for hiking and scenic overlooks. Its 12 miles of marked trails, and the park lodge’s unforgettable stone terrace both provide some of the best and most iconic scenery within the Illinois River Valley.
Grafton is also home to a number of bars and riverfront restaurants, which often hold seasonal tastings and live music on weekends. The Loading Dock is a renowned choice with a sizable patio boasting unobstructed views over the river. Just note that summer hours at this often busy joint last only until October before shorter winter hours kick in.
Nauvoo
Nauvoo is another wonderful small town along the banks of the Mississippi River in western Illinois. Its grid of preserved buildings from almost two centuries ago, many of which are tied to its early Mormon settlers, provides a nice backdrop for pleasant walks downtown, particularly when the leaves begin to change in September and October. Make sure to take a look at the Joseph Smith Historic Site and Nauvoo State Park, both of which will teach you a bit more about this town's unique past, one that is, of course, heavily interlinked with Mormonism.
You can opt to engage with a variety of community events during this time of the year, namely the Pumpkin Walk in October, a celebration that transforms Mulholland Street into an illuminated display of carved pumpkins, a local tradition that draws families from across the region. The area is also well known for its vineyards, with a very popular grape festival taking place every Labor Day weekend. Even after the grape-themed event ends, spots like Baxter's Vineyards & Winery sit just outside of town and accept visitors well into the year.
Monticello
Monticello in central Illinois is a beautiful countryside community that is full of parks, gardens, woodland trails, and wide meadows in and around it. Cool locales like the Allerton Park & Retreat Center combine natural scenery with large-scale art and architecture, including classical statues and garden ornaments set against turning leaves.
The town itself maintains a traditional courthouse square with independent shops, eateries, and historic landmarks at practically every nearby corner. Each September, the nearby Monticello Railway Museum operates the “Railroad Days” event, and throughout October, the museum schedules fall-themed train rides through the surrounding countryside. These excursions do a great job of highlighting the abundant farmland fields and woodlots of Piatt County in full color. For residents of nearby Decatur who want a quieter place to enjoy autumn in 2025, definitely pay a visit to Monticello for an afternoon or two before it gets too cold.
Make the Most of Fall in Illinois this Year
Illinois clearly offers a wide range of destinations that are complemented by the fall, from riverside towns framed by rolling hills to small communities surrounded by farmland and forest. Each of the spots above provides its own way to experience the season, whether through hiking trails, scenic drives, or local festivals tied to harvest traditions. Timing a visit between late September and late October ensures the best views of changing leaves across the state. For travelers of all kinds, these towns show how Illinois beautifully combines natural scenery with local culture during autumn.
