The 10 Most Charming Small Towns in Illinois

As the world starts to open up post-pandemic, chances are you’re starting small: small gatherings with friends, limited seating in restaurants, and even short trips closer to home—which is why a weekend getaway to a quaint small town is the perfect way to ease back into traveling. Or perhaps you—like so many others—are considering making a permanent move out of the city to take advantage of more space, breathtaking nature and cheaper cost of living. While you may not see an onslaught of other people in these little Illinois towns, you’ll still find a throng of things to do, from visiting a stop along the Underground Railroad to whizzing around a racecar track. Read on to choose your next travel destination.

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© Photography by Bob Hallam/Getty Images

Image credit: Photography by Bob Hallam/Getty Images

1. Galena, IL

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.

Where to stay:

  • Lake view cottage: sleeps 4
  • Westview escape: sleeps 10
  • Bravarian brew house: sleeps 6

© Gary Todd/Flickr

Image credit: Gary Todd/Flickr

2. Woodstock, IL

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. Yes, the entire downtown is on the National Register of Historic places, and that hasn’t changed (try exploring it on a self-guided walking tour), but there are plenty of interesting places to swerve, too. Dip into the Woodstock Opera House to hear a jazz quartet or catch a musical (pandemic reopening protocols pending), 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.

Where to stay:

  • The Chicken Coop Inn: sleeps 2
  • Angel Loft: sleeps 4
  • Golf getaway: sleeps 12

© Bruce Leighty/Getty Images

Image credit: Bruce Leighty/Getty Images

3. Princeton, IL

What’s more picturesque than a covered bridge? Two covered bridges, which sit just a smidgen outside of Princeton’s city limits. The historical preservation around Princeton doesn’t stop there: In addition to a classic, old-timey main street, the town is also home to the Lovejoy Homestead, a stop on the Underground Railroad that will reopen for tours after the pandemic is officially over. Until then, you can still roam its grounds while reading more about the homestead’s history.

Where to stay:

  • Country home: sleeps 7
  • Rustic valley cottage: sleeps 8
  • Rejoice Inn: sleeps 3

A post shared by Dairyhaus Homemade Ice Cream (@dairyhaussocial)

This village near the Illinois/Wisconsin border is dotted with buildings from the 1800s, many of which feature distinctive limestone facades—including the Dairy Haus, an ice cream shop with a devoted following in the area. (Bourbon praline? Wedding cake? A scoop of each, please!) While you’re in the area, don’t forget to hop over the border—just a couple of miles away—to stock up on New Glarus beer, another treat with a cult following that’s sold only in Wisconsin. Need something other than treats to stir up some excitement? Blackhawk Farms Raceway, in the neighboring town of South Beloit, welcomes spectators of car and motorcycle races, and offers the occasional driving school if you’d rather take the wheel yourself.

Where to stay:

  • Cozy cottage: sleeps 10
  • Traveler’s sanctuary: sleeps 4
  • Country guesthouse: sleeps 8

© Ken Lund/Flickr

Image credit: Ken Lund/Flickr

5. Nauvoo, IL

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.

Where to stay:

  • Ten Acre treehouse: sleeps 6
  • Newly furnished brick house from 1842: sleeps 10
  • Pioneer home: sleeps 8

© Todd Ryburn Photography/Getty Images

Image credit: Todd Ryburn Photography/Getty Images

6. Ottawa, IL

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.

Where to stay:

  • Tranquility at RiverZen: sleeps 5
  • Panoramic views of the harbor: sleeps 6
  • 20 minutes from Starved Park Rock: sleeps 4

A post shared by The District Quincy (@thedistrictquincy)

Quincy is chock full of social-distancing-friendly activities that are fun in and of themselves. 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 on 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.`

Where to stay:

  • Peaceful country cottage: sleeps 6
  • Historic mansion built in 1910: sleeps 8
  • Guest house on the river: sleeps 4

© City of Fulton

Image credit: City of Fulton

8. Fulton, IL

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.

Where to stay:

  • The River House: sleeps 6
  • Home on picturesque Mississippi River: sleeps 4
  • The Stephenson at Mount Moriah: sleeps 8

© nycscout/Flickr

Image credit: nycscout/Flickr

9. Lebanon, IL

This is Illinois’ OG college town: McKendree College is the oldest in the state. There’s plenty to learn about even off campus, from the histories of the city’s buildings (a surprising mix of Southern Colonial, Greek Revival, Gothic and other styles) to the Emerald Mound, the preserved remains of a Native American village and effigy mounds. Is that not enough history for you? Check out the Mermaid House, a former hotel visited by Charles Dickens, who later name-dropped it in American Notes.

Where to stay:

  • Quiet villa: sleeps 7
  • Entire home new St. Louis: sleeps 5
  • Barn loft: sleeps 4

© Arcola Chamber of Commerce/Facebook

Image credit: Arcola Chamber of Commerce/Facebook

10. Arthur and Arcola, IL

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. (Keep an eye out—Raggedy Andy turns 100 this year, and celebrations may pop up.) 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 upon while admiring the farm’s llamas, exotic chickens and other animal residents.

Where to stay:

  • Sister’s cottage: sleeps 6
  • Cozy two-bedroom apartment: sleeps 6
  • Cape Cod style home: sleeps 10

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