6 Romantic Small Towns In Illinois For A 3-Day Weekend

Those looking for a romantic getaway in Illinois need look no further than these picturesque small towns to enjoy a 3-day weekend with your loving partner or spouse. Illinois is a land flowing with wine, quirky photo ops, and artsy communities, which make for many date night ideas.

In these romantic small towns, you can grab funny photos at the largest rocking chair in a small town, sip wine while hiking the trails of Shawnee National Forest, slow down and learn natural healing methods from hippies, or get lost in an outdoor labyrinth together.

Learn more about six romantic small towns in Illinois to consider for a 3-day weekend.

Makanda

Makanda is a hippie paradise hidden away in Southern Illinois. In the 1970s, musical artists such as Dave Dardis moved to this peaceful small town, and with it, other hippies followed, giving it a cute, artsy vibe that matches well with its beautiful landscapes. For adventurous couples, along Makanda's historic boardwalk, there is Healing Traditions Massage and Yoga, offering healing massages, BioDynamic Cranial Sacral Therapy, and other services.

For hippie-inspired treasures, consider picking up a piece of art from the Rainmaker Art Studio with your loved one, or savor local wine from the beautiful Blue Sky Vineyard, which is modeled after a Tuscan Villa. If you are the hiking sort, you and your partner can experience the beauty of nature at the Giant City State Park, noted for its bluffs, waterfalls, and red cedar trees. To get the full Makanda experience, rent a cabin with Makanda Inn & Cottages.

Pomona

Pomona is a great getaway for anyone looking to escape into nature or sample the local wines. Situated within the Shawnee National Forest, it is a perfect place for couples looking to go hiking or take a scenic drive. Within city limits, you can go to the Pomona Natural Bridge, a 90-foot-long and 30-foot-high sandstone bridge that was formed through water erosion. Another nearby trail is the Little Grand Canyon Trail, with beautiful views of the Big Muddy River.

If you are not up for a hike, go for a drive on the Bald Knob Wilderness in nearby Alto Pass, a majestic place within the Illinois Ozarks. Pomona is most well known for its Shawnee Hills Wine Trail, with several wineries nestled in the woods like Pomona Winery and Hickory Ridge Winery. There is a Wine Trail Wilderness campground that is renowned for its close proximity to the wineries and its beautiful fields of wildflowers. For a place to stay, consider renting a rustic but comfortable cabin with CornerStone Cabins.

Woodstock

You don't have to travel far outside of Chicago to find a beautiful small town for a romantic getaway. Situated about 60 miles northwest of the big city is Woodstock, which has received honors for being a "distinctive destination" with its classy architecture, diverse orchards, and festivals. One of the most romantic places in Woodstock is the 1889 Woodstock Opera House. This downtown structure regularly puts on shows from musical tributes to comedic acts and even artistic exhibitions.

Woodstock overflows with orchards and gardens for romantic strolls or picking fruit to eat. One such place is the delightful Mariposa Meander, a garden with benches and paths to chat while you look at the flowers. Another is Homestead Orchard, a family-run apple orchard featuring an 1880s horse barn that sells antiques and candles. If you take your trip in July, you can enjoy the Woodstock Folk Festival with local and international performers. For a good place to stay, consider the Cherry Branch Guest House, a B&B just a few blocks away from Woodstock's historic square.

Macomb

Couples who enjoy a good game night will both love Macomb. This town boasts the world's largest Monopoly board called Macombopoly. By downloading an app, you can play a game on Macombo's Courthouse Square, which includes multiple Monopoly-themed sculptures from Abraham Lincoln's stovepipe hat to a spinning device and a "jail" spot where the old Macomb Jail once stood.

There are plenty of other quirky attractions surrounding Macomb for you and your partner to try out, from petting alpacas at the Little Creek Alpacas Farm to figuring your way out of a maze at the Prairie Labyrinth within the Lakeview Nature Center. There are a few chain hotels in town, or if you are willing to drive 20 minutes to Plymouth, you can stay at a Queen Anne mansion at the Plymouth Rock Roost Bed & Breakfast.

Casey

Some of the best romantic getaways have excellent photo ops to remember your trip years down the road. There is no town in Illinois with as many quirky spots as Casey. It is home to the Big Things in a Small Town roadside attraction, which includes a multitude of massive items that have won awards from the Guinness Book of World Records. For example, there is the World's Largest Wooden Shoe at the Whisk + Lollies Bakery and Candy Shoppe, or the World's Largest Rocking Chair, Wind Chime, Truck Key, and much more. Many of these items are located near great places to eat, such as the World's Largest Pitchfork right beside Richards Farm Restaurant. You can go for a lovely stroll by the lake at Fairview Park, which also provides campgrounds. For good accommodations, go to the Eighteen-Ninety Sleepover hotel.

Galena

Situated on the Mississippi River, Galena is a lovely arts town that has a little something for every couple. Are you into old-fashioned date nights? Then the American Old Fashioned Ice Cream Parlor is right for you, an old-timey restaurant with a wide selection and generous portions. If you want a dinner and a show in an intimate setting, then Amelia's Under the Lamplight Dinner Theatre is just right for you. For couples who prefer the macabre side of life, they can experience it by visiting A Darkness Lovely, which features gothic decor and gifts, and also offers haunted town tours through Haunted Galena Tour Co.

For a pleasant walk with your loved one, go to the Casper Bluff Land & Water Reserve, an 85-acre preserve with wonderful views of the Mississippi River bluffs. Stay at the romantic 305 North Inn Bed & Breakfast, situated off the town's historic Main Street.

A Little Something for Every Couple

These Illinois communities have a little something for every couple. Outdoorsy couples can go exploring the canyons and trails of Pomona, while those who prefer quirky roadside attractions can snap photos of all the big items in Casey. For gothic lovers looking for a truly haunted experience, Galena is just right. Almost all of these towns also have charming bed & breakfast inns to enjoy a more intimate stay. No matter what your tastes, one of these towns will be just right for your romantic 3-day weekend in Illinois.