If you're planning a romantic fall getaway, you want more than just pretty leaves — you want a destination that feels like it was made for slowing down together. McHenry County, just an hour northwest of Chicago, delivers exactly that: orchards filled with apples, wetlands turning gold, and downtowns that still feel like they belong in a movie (because a couple of them have been). Here's how to spend it.
Apple Picking in McHenry County's Orchards
Nothing says fall in McHenry County quite like apple picking and All Seasons Orchard in Woodstock does it right. With more than 11,000 trees and 12 varieties — from crisp Honeycrisp to the lesser-known Asian pear — there's a bushel for every taste. Wander the rows together, then reward yourselves at the farm market, where homemade apple cider donuts are the real reason people keep coming back.
For a bigger production, Stade's Farm Market in McHenry runs weekend fall festivals from early September through the end of October, complete with a 30-acre pumpkin patch. It's less quiet-afternoon-for-two and more full-day-adventure — plan accordingly.
Raise a Glass at McHenry County's Craft Breweries
McHenry County's craft beer scene has quietly become one of its best-kept secrets, and two stops make for the perfect fall pairing. At Kishwaukee Brewing in Woodstock, brewmaster Dan turns out German pilsners, English bitters, and a rotating cask tapped fresh every Friday — settle onto the patio and let the afternoon go slow. Craving something a little closer to downtown? Crystal Lake Brewing pours its flagship Beach Blonde golden lager just steps from the Metra, with food trucks rolling through most weekends to keep the good times and good food coming.
Hiking and Kayaking in McHenry County
Not every moment calls for a crowd. Moraine Hills State Park offers flat, easy trails that wind past wetlands and glacial kettle lakes — find a bench, take in the view, and let the leaves do the talking. Or head to Cary Lake at Rotary Park, where Midwest Kayak Rentals will get you paddling across water that mirrors the color overhead. Circle the lake, then finish with a walk along the shoreline trail.
Fall for the Woodstock Square
If you've seen "Groundhog Day," you've already seen the Woodstock Square — this is where Bill Murray relived February 2nd on repeat, and where Chester Gould dreamed up Dick Tracy decades before that. Today, the Woodstock Opera House, built in 1889, anchors the downtown built for wandering hand in hand, and Squire on the Square, set inside the historic Old Courthouse Center, makes an easy pre-show dinner.
Autumn Drive: McHenry County's favorite weekend!
Time it right and your trip could land on Autumn Drive, McHenry County's 38th annual fall tradition, running October 16 - 18, 2026, through the country roads of rural Woodstock and Marengo. Pick your own apples, browse antiques and crafts from farm to farm, and stock up on honey and jam along the way. Admission is free, rain or shine, and yes — there's an app for that, so download the Naturally McHenry County app on iOS or Android before you hit the road.
Plan Your Romantic Fall Weekend: Sample Itineraries
Full Saturday -
- Morning: All Seasons Orchard for apple picking and cider donuts
- Early Afternoon: Lunch and a flight at Kishwaukee Brewing
- Late Afternoon: Hike through Moraine Hills before the light goes
- Evening: Dinner at Squire on the Square
A Slower Weekend -
- Friday Evening: Walk the Woodstock Square, catch a show at the Opera House
- Saturday Morning: Kayak Cary Lake at Rotary Park
- Saturday Afternoon: Autumn Drive if the dates line up, or Stade's Farm & Market if they don't
- Sunday: Coffee at Aroma Coffee & Wine, a matinee at Raue Center, and a quick round at Crystal Lake Brewing before heading home
Half-Day Add-On
Already in the area for something else? Moraine Hills plus Kishwaukee or Crystal Lake Brewing makes a solid three-hour outing, no full day required.
Best Time to Visit McHenry County for Fall Colors
Peak color in McHenry County arrives mid to late October, so if you can wait, the late-month color is worth it. October weekends around Autumn Drive draw a crowd, so save the orchards for a weekday morning if you'd rather have the trees to yourselves.
And pack layers. Mornings at the orchard run cold, afternoons on the water run warmer than you'd think, and evenings on the Woodstock Square drop fast once the sun's down.
Frequently Asked Questions
- What is the best time to visit McHenry County for Fall Color?
- Peak color in McHenry County typically arrives mid to late October, so if you can wait, the late-month color is worth it. October weekends around Autumn Drive are usually the most colorful!
- Where can we go if we want something quiet and peaceful?
- Moraine Hills State Park and Cary Lake at Rotary Park are your best bets for slowing down without a crowd. Moraine Hills brings easy trails and wetland views made for a bench and a long look; Cary Lake adds a kayak and a shoreline walk to close it out.
- Which apple orchard fits a couple better than a family day trip?
- All Seasons Orchard in Woodstock is a classic pick — rows of trees, dozens of apple varieties, cider donuts, and photo ops galore. Stade's Farm & Market is the better call if you'd rather turn the day into a full fall festival, pumpkin patch included.
- If we want to make it a weekend trip, where can we stay?
- McHenry County has a variety of local hotels that are centrally located. The Hampton Inn McHenry and Holiday Inn Crystal Lake are close to many attractions and make for a comfortable stay.