The 11 Most Charming Small Towns in Illinois

• Why We Recommend It: historic, winter activities, vibrant town life, arts and culture
• Where to Stay: Lake view cottage; Private Home on Wooded Lot; Irish Cottage Inn & Suites

Galena. Heard of it? OK, yes, you have—it has Oprah’s stamp of approval as one of the most charming small towns in the country, among other accolades—but it’s so well-known for a reason. While its streets are steeped in history (Ulysses S. Grant famously called the town home, and Lincoln and Douglas gave speeches on the balcony of the DeSoto House Hotel, which still stands today), Galena is anything but a sleepy small town. Instead, it’s bustling with wineries, galleries, ghost tours and even some gnarly snowboarding slopes.

• Why We Recommend It: historic, good eats, arts and culture
• Where to Stay: The Chicken Coop Inn; Historic Woodstock Square Apartment; Hampton Inn McHenry

Woodstock is famously the town where Groundhog Day was filmed, but no two days here are the same when you explore everything it has to offer. In fact, the entire downtown is on the National Register of Historic Places and can be appreciated in full with a self-guided walking tour. There are many other interesting spots to explore, too. Dip into the Woodstock Opera House to hear a jazz quartet or catch a musical, pop by one of several local farms and orchards to pick in-season produce or take a tour of world cuisines as you stroll past Woodstock’s many diverse restaurants.

• Why We Recommend It: historic sites, good for shopping, scenic
• Where to Stay: Rustic valley cottage; Covered Bridge Cottage; AmericInn by Wyndham Princeton II

What’s more picturesque than a covered bridge? Answer: Two covered bridges, and you can find ‘em just a smidgen outside of Princeton’s city limits. The historical preservation around Princeton doesn’t stop there—the old-timey main street features numerous shops and antique malls, and the town is also home to the Lovejoy Homestead, a stop on the Underground Railroad that visitors can tour for a little Civil War education. Plus, Princeton also boasts numerous scenic bike trails for the active types in your travel party.

• Why We Recommend It: historic, natural beauty, outdoor recreation
• Where to Stay: Ten Acre treehouse; 1880 Sonora Town Hall Cottage; Nauvoo Grand Bed & Breakfast

Calling all history buffs: Nauvoo, IL is a small town with a big impact on the history of Mormonism. While Joseph Smith and other prominent founding members haven’t called the city home since the late 1840’s, it’s still easy to take a trip to the past with help from an array of historical reenactors, who show off blacksmithing techniques and brick-making (you can take one home as a souvenir). Don’t miss the extensive self-guided walking tour of notable Nauvoo buildings to help your imagination travel through time, too. Your visit isn’t complete until you’ve walked the grounds of the Nauvoo Temple, either; beyond its beautiful design, this stately building also happens to be the only LDS-owned temple with a bell tower. And if you feel like spending some time in nature, some gorgeous scenery—a pristine lake surrounded by woods—awaits at Nauvoo State Park, too.

• Why We Recommend It: geological attractions, outdoor recreation, scenic, historic architecture, historic sites, artsy vibes
• Where to Stay: Tranquility at RiverZen; Private Wooded Escape; Hampton Inn

Nearby Starved Rock State Park may steal the spotlight from Ottawa, but it’s well worth trekking into town after you’ve finished your hike. Studded with well-maintained Victorian homes (and with the requisite charming downtown you’d expect on this list), Ottawa puts its own twist on the small-town experience with an abundance of modern murals to mix the old with the new. And if you need a snack to power you through another round of Lincoln/Douglas historical sites, keep an eye out for the beloved Popcorn Wagon, a relic from the 1890s that still serves up fresh, salty kernels.

• Why We Recommend It: arts and culture, mid-mod architecture, wildlife viewing, good eats
• Where to Stay: Arlene’s Retreat; Historic mansion built in 1910; Town & Country Inn and Suites

Quincy is chock full of fun activities: Take yourself on a driving tour of the city’s smattering of mid-century modern homes, or follow this guide to public art installations, which also includes tips on where to grab curbside food and drink as you go, so you can create your own combination art and pub crawl. Had your fill of murals and snacks? Check out one of the prime lookout spots for seeing bald eagles when they spend the winter in the area. But even if you manage to see every home, mural, and fowl in Quincy, you’re still in luck: Hannibal, MO—and its treasure trove of Mark Twain attractions—is just half an hour and a hop across the Mississippi away.`

• Why We Recommend It: historic attractions, Dutch culture, water activities
• Where to Stay: Home on picturesque Mississippi River; Rock River Retreat; AmericInn by Wyndham

Fulton provides another opportunity to step back in time, but with a distinctly Dutch vibe. Admire the city’s prominent windmill, brought over from the Netherlands, and pop into the gift shop to take home the buckwheat, rye, and other grains ground on-site. From there, take a walk through Heritage Canyon, which is home to pioneer-era structures such as a one-room schoolhouse and a covered bridge. If you’re in the mood to live in the moment instead, explore your options for boating and fishing along the Mississippi River.

• Why We Recommend It: scenic, arts and culture, farmstay vibes
• Where to Stay: Sister’s cottage; Cape Cod style home; Unique Suites Hotel

These delightful villages sit just a few miles apart on Highway 133 in Illinois’ Amish country, and if you’re going to visit one, it would be a shame to miss out on the other while you’re so close by. Arcola may be slightly better known, as it’s where the Raggedy Ann doll was first invented around the turn of the 20th century. Another site to see in town? The “World’s One and Only Hippie Memorial,” a public folk art installation dedicated to the tumult of the 1960s. Meanwhile, in Arthur, The Great Pumpkin Patch awaits with 300+ varieties of squash and gourds grown on-site, plus a variety of baked goods to snack on while visiting the farm’s llamas, exotic chickens and other animal residents.

• Why We Recommend It: historic, parks, water activities, picturesque
• Where to Stay: Private 25-Acre Estate; Aviation Lover’s Country Home; Best Western Geneseo Inn

This Henry County gem is easily accessible—the famous Route 6 runs right through it—and boasts a number of low-key attractions, including a particularly quaint and old-timey downtown strip, numerous residential enclaves featuring impeccably restored Victorian homes on tree lined streets and a picturesque river and canal just outside of town where tubing, fishing and kayaking opportunities abound. There’s also a historical museum devoted to the town’s past as an underground railroad hideout, plus 100 acres of green parkland to explore and five different playgrounds for those traveling with kids in tow. Bottom line: If you’re looking for a quiet stay with boatloads of Norman Rockwell charm, Geneseo is hard to beat.