Day Trip Itineraries

OREGON DAY TRIP 1

OUTDOOR ESCAPE

Start the day with a cozy breakfast at Bela’s Cafe.
Visit Nachusa Grasslands, a 4,100-acre preserve and one of the most biologically diverse grasslands in Illinois. The Grasslands offer the opportunity to hike through the prairie, bird watch, identify native grasses, flowers and trees and see the bison roam. The visitor’s center is open daily from dawn to dusk.
For lunch, stop by Jen’s Artisan Breads for a charcuterie box and a loaf of fresh bread. Take it to the riverfront at Carnation Park and enjoy a picnic lunch.
After lunch, pedal through Carnation Park’s bike trails or fish along the riverbank.
Fish along the riverbank at Carnation Park or pedal through Park West.
Don’t forget your fishing license!
End the day with dinner at LaVigna, a Northern Italian eatery near the river.
Want to make it a weekend trip? Reserve a one-room cabin at White Pines Forest State Park.

OREGON DAY TRIP 2

Start the day with a hike at White Pines Forest State Park where trails range from a light 1-mile loop to a 2.6-mile hike with bridges, buttes and breathtaking views from various elevations.
If you’ve built up an appetite, you don’t have to leave White Pines for lunch! Stop by the Lodge Restaurant for homestyle cooking.
Enjoy time in the afternoon sun while you float down the Rock River with White Pelican Canoe and Kayak Rental. Open seven days a week, White Pelican offers self-guided trips down the Rock River in a watercraft of your choice: tubes, kayaks, canoes and stand-up paddle boards are available. Routes range from 4-19 miles. Custom routes, parties and overnight trip options are available.
To round out the day, enjoy a drink and live music at Chrissy’s Corner or a cigar at Bad Ash Cigar Lounge. Then, grab a bite to eat at The Hunt Club, a unique taphouse along the river.
Want to make it a weekend trip? Camp at Lowden State Park at one of 80 campsites or make your float trip an overnight adventure.

OREGON DAY TRIP 3

Start your day at the renowned Lorado Taft Blackhawk Statue—the first stop on Oregon’s Sculpture Trail, which includes 19 sculptures, four by Lorado Taft.
After you’ve completed the trail, stop for lunch at Ogle County Brewery. Meander through their entryway, where historical artifacts from Oregon are on display.
For your afternoon in Oregon, take a short walk down the road to the Coliseum Museum of Art, Antiques and Americana (CMAAA) and explore its galleries, which feature national, regional and local artists. Next, visit the Oregon Public Library—a Carnegie library featuring the Eagle’s Nest Art Gallery on the second floor. If you’re up for one more stop, swing by Ukulele Station America, a magnet for ukulele players across the nation housed in a small stone cottage.
End the day with a stroll through the commercial historic district and spot public art along the way (tip: check The Village Bakery, Merlin’s Greenhouse and the Oregon Chamber of Commerce building for murals!).
Want to make it a weekend trip?
Stay at the Paddle Wheel Inn.

OREGON DAY TRIP 4

Fuel up for the day with pastries and donuts at The Village Bakery (Be sure to check out the side of the building for a beautiful mural!).
Stroll through downtown, officially known as the Oregon Commercial Historic District, and visit local boutiques, like White Pine Mercantile and VicariouStyle and the local-favorite Merlin’s Greenhouse.
Grab lunch at Toasty Noodles, a casual noodle restaurant serving ramen, sushi and poke.
Then, spend your afternoon meandering through Conover Square Mall and explore a variety of vendors selling antiques, collectibles and more.
Stop for drinks at Cork & Tap, a cozy pub with housemade cocktails, beer and wine flights. They even have board games if you’re up for some friendly competition over a drink!
End the day at the Blackhawk Steak Pit, a local favorite serving steak and seafood with a supper club atmosphere.
Want to make it a weekend trip?
Stay at Lincoln Way Stay.

OREGON DAY TRIP 5

Park West has something for everyone to enjoy! Stroll or bike the winding paths, play on the playgrounds or splash pad, or enjoy a friendly competition: there are pickleball, tennis, basketball and sand volleyball courts, plus a skate park and mini pitch.
Take a break from play and have lunch at Jay’s Drive-In, a 60s-themed restaurant. Eat in their dining room, on the patio or in your car—car hops will bring your food to you!
Parents, if you need an extra dose of caffeine, stop by Hazel’s for an iced latte!
After lunch, visit Stronghold and explore a Tudor-style castle! Stronghold also features a disc golf course. If the family is up for more adventure, head to BerryView Orchard or Granny’s Berries to pick your own fruit (seasonal availability).
If it’s a rainy day, adventure inside at The Rink, a roller rink and arcade in nearby Mt. Morris.
End the day with pizza or pasta from Alfano’s Italian.
Want to make it a weekend trip?
Find an Airbnb for the family in Oregon.