Main Street Galena, Illinois. Image credit Dawid S Swierczek via Shutterstock.

10 Picturesque Small Towns in Illinois for a Weekend Retreat

Admitted to the Union in December’1818 as the 21st state, Illinois, situated in the American Midwest, is acclaimed for its dramatic terrain, rich heritage, enchanting attractions, and welcoming locals. Nevertheless, whenever one thinks of vacationing in the Prairie State, its most widely known city Chicago is the first to hog all the limelight from holidayers. But the innumerable picturesque small towns dotting the state have so much more to offer than this ‘global city.’ For those wishing to escape from buzzing urban cities or seeking time to relax after a hectic work schedule, these small towns in The Land of Lincoln are ideal for a quaint weekend getaway.

Galena

Quaint Shops on the Main Street of Galena, Illinois.
Quaint Shops on the Main Street of Galena, Illinois, via Wirestock / iStock.com

Galena, called after the natural mineral form of lead (II) sulfide, is the seat of Jo Daviess County situated in the far northwestern corner of the state along the Galena River (one of the many tributaries of the Mississippi River). This erstwhile bustling port town is currently a favored destination for its spectacular rolling hills, historic 19th-century architecture, specialty shops, art galleries, restaurants, hotels like Irish Cottage Inn & Suites, and world-class resorts such as WorldMark Galena, Eagle Ridge Resort & Spa, and Chestnut Mountain Resort. With more than 800 National Register-listed properties, about 85% of the town is a part of the 581-acre Galena Historic District. Some noteworthy sites of interest include the Old Market House State Historic Site, Elihu Benjamin Washburne Home, Belvedere Mansion, Dowling House, the restored Ulysses S. Grant Home, Galena/Jo Daviess County History Museum, Saint Michael’s Catholic Church, and Galena Arts & Recreation Center. Annually, the town hosts celebrations like the County Fair in Grant Park, and Halloween Parade.

Princeton

Colorful old brick buildings and storefronts in downtown Princeton, Illinois
Colorful old brick buildings and storefronts in downtown Princeton, Illinois

Princeton, the county seat of Bureau County, is situated on the southern side of Interstate 80, about 100 miles southwest of Chicago. It features a historic downtown, over 200 acres of parks, a public golf course, and hosts the annual Homestead Festival on the second weekend of September, offering activities for all ages. Main Street is lined with numerous independent shops, bars, and restaurants, with its southern end serving as the historic retail core, home to the courthouse, Apollo Theater, major bank branches, the notable Matson Library, the Bureau County Historical Society, and many service businesses. The northern end of Main Street is known as “The Art District,” which includes its commercial area, the Amtrak station, upscale clothing stores, and a park. Visitors can stay overnight at well-known hotels such as AmericInn by Wyndham Princeton IL and Super 8 by Wyndham Princeton.

Geneva

Overlooking Island Park in Geneva, Illinois.
Overlooking Island Park in Geneva, Illinois.

Geneva, the administrative center of Kane County, is a popular tourist destination situated along the scenic Fox River, approximately 36 miles west of downtown Chicago. The town boasts over 160 specialty shops and inviting eateries, offering visitors excellent shopping and dining options. Outdoor enthusiasts, especially cyclists, can explore sections of the multi-use Fox River Trail and the Illinois Prairie Path that run through Geneva. Key attractions include the Fabyan Windmill, Riverbank Laboratories, Sacred Heart Seminary Shrine, Island Park, Fabyan Villa Museum, Elizabeth Place, and the Geneva History Museum. The town also hosts annual events such as the Geneva Arts Fair, Swedish Days, Christmas Walk, and Festival of the Vine. After a busy day, visitors can relax at accommodations like the Comfort Inn & Suites, Herrington Inn & Spa, or Oscar Swan Country Inn Bed & Breakfast.

Nauvoo

Downtown Nauvoo, Illinois.
Downtown Nauvoo, Illinois. Image credit: Ken Lund via Flickr.com

Home to only 950 inhabitants as per the latest US Census, Nauvoo occupies a wide bend of the Mississippi River in western Illinois’s Hancock County, approx. 30 miles southwest of Burlington, Iowa. Originally a prosperous settlement of early Mormon pioneers, the town’s meticulously maintained landmark structures provide a glimpse into its glorious past. Tourists must take a tour through the Nauvoo Historic District in horse-drawn carriages and visit some of the awe-inspiring contributing properties in the district such as the Nauvoo Illinois Temple, Joseph Smith Homestead, Brigham Young Home, Nauvoo House, Joseph Smith Mansion House, etc. Nauvoo Grand Bed & Breakfast, Nauvoo Temple House Hotel, and Willard Richards Inn are ideal for resting overnight, while nature lovers can unwind in the peaceful surroundings of the 148-acre Nauvoo State Park.

Ottawa

Reddick Mansion sitting in the historical park of Ottawa, Illinois.
Reddick Mansion sitting in the historical park of Ottawa, Illinois. Editorial credit: Dawid S Swierczek / Shutterstock.com

LaSalle County’s administrative hub and the main community of the Ottawa, IL, Micropolitan Statistical Area, this small town is situated in north-central Illinois at the confluence of the Fox and Illinois Rivers, approximately 80 miles southwest of Chicago. Renowned for its abundant natural resources and rich heritage, Ottawa welcomes visitors to its charming downtown, filled with historic buildings, cozy cafes, antique shops, unique boutiques, restaurants, and accommodations like Hampton Inn Ottawa, Fairfield Inn & Suites Ottawa, and Super 8 by Wyndham Ottawa. Key attractions include the Reddick Mansion, Fisher-Nash-Griggs House, Ottawa Historical & Scouting Heritage Museum, and the historic site of the Lincoln-Douglas debate at Washington Square Park. From Ottawa, travelers can easily access Starved Rock State Park, famous for its sandstone cliffs, waterfalls, deep canyons, and extensive trails for hiking and horseback riding. The park also offers camping, ice skating, fishing, cross-country skiing, boating, and wildlife observation opportunities.

Woodstock

Downtown Woodstock, Illinois
Downtown Woodstock, Illinois. Image credit Nejdet Duzen via Shutterstock

Woodstock, originally called ‘Centerville’ due to its central location in McHenry County, lies about 45 miles northwest of Chicago. Recognized by the National Trust for Historic Preservation as one of the “Distinctive Destinations,” it is celebrated for its historic town square and downtown area from the turn of the century. The town square is dominated by the Woodstock Opera House and Old McHenry County Courthouse and is filled with numerous shops, cafes, art galleries, bars, and restaurants. Accommodations like AmericInn by Wyndham Woodstock II, Cherry Tree Inn Bed & Breakfast, Quality Inn & Suites Woodstock, and Super 8 by Wyndham Woodstock IL serve visitors. Tourists can also enjoy walking tours of filming sites from the classic American movie “Groundhog Day.” Throughout the year, residents and visitors participate in events such as the Fair Diddley Art Fair, Groundhog Days, Midwest Mozart Festival, Festival of Lights, Victorian Christmas, and summer band concerts.

Fulton

De Immigrant Windmill in Fulton, Illinois.
De Immigrant Windmill in Fulton, Illinois. Image credit: EJRodriquez - stock.adobe.com.

Fulton is a charming river town named after Robert Fulton, a distinguished American engineer and steamboat inventor. Located in Whiteside County, it lies directly across the Mississippi River from Clinton, Iowa. Besides its stunning Mississippi River views, Fulton is celebrated for its Dutch heritage, with residents annually hosting the Dutch Days Festival on the first weekend of May. The town features notable attractions such as the De Immigrant Windmill, Lock & Dam 13 Recreation Area, Martin House Museum, Windmill Cultural Center, Heritage Canyon, and the Andresen Nature Center. Visitors can enjoy stays at acclaimed hotels like AmericInn by Wyndham Fulton Clinton, Country Inn & Suites by Radisson, Clinton, IA, and Holiday Inn Express Hotel & Suites Clinton. Nearby Morrison Rockwood State Park offers a large campground, along with plentiful boating and fishing in Lake Carlton.

Lebanon

Singer on the streets of Lebanon, Illinois.
Singer on the streets of Lebanon, Illinois. Image credit RozenskiP via Shutterstock.

This picturesque St. Clair County town labeled after its namesake Eastern Mediterranean country forms a part of the Greater St. Louis metropolitan area’s Metro-East region. Lebanon is home to the main campus of McKendree University, Illinois’s oldest higher educational institution founded by pioneer Methodists in 1828. History buffs must survey the Emerald Mound & Village Site, Mermaid House Hotel, and Lebanon Historic District. The town’s main commercial district draws tourists with its eclectic mix of antique stores, independent shops, locally-owned restaurants, and bed & Breakfasts like Lebanon’s Queen Anne. Additionally, spend some quality time at the Horner Recreational Park, enjoy a concert, play, or listen to speeches by esteemed contemporary speakers at The Russel E. and Fern M. Hettenhausen Center for the Arts, and watch excellent theatrical performances at the Looking Glass Playhouse.

Quincy

Downtown street in Quincy, Illinois.
Downtown street in Quincy, Illinois. Image credit Sabrina Janelle Gordon via Shutterstock

Illinois’s “Gem City,” Quincy, the Tri-State region’s leading hub, and Adams County's government seat, is situated in the state’s western portion along the Mississippi River and Quincy Bay. The town’s Downtown Historic District perfectly amalgamates well-preserved late 19th-century and early 20th-century architecture with modern-day shopping, entertainment, and eating joints. Vacationers can take a stroll along the waterfront that serves as a venue for numerous events throughout the year, or tour the Quincy Society of Fine Arts, Quincy Museum, South Side German Historic District, Villa Kathrine, and Quincy Park District’s 26 parks. Merrymakers must not miss the town’s annual celebrations like the Dogwood Parade & Festival, Art Fest & Folk Life Festival on Maine Street, and Q-Fest at Washington Park. The Town & Country Inn and Suites, Stoney Creek Inn, and Microtel Inn & Suites by Wyndham Quincy provide holidayers with outstanding facilities.

Mount Carroll

Historic District in Mount Carroll, Illinois
Historic District in Mount Carroll, Illinois

Mount Carroll, christened after Charles Carroll of Carrollton, an endorser of the Declaration of Independence, is a teeny town in the state’s extreme northwestern corner. A major portion of the downtown and older residential area of this administrative center of Carroll County forms a part of the 118-acre National Register-listed Mount Carroll Historic District. The District contains three chief sections: a traditional downtown which includes a courthouse, a business district, and a library; a residential area to the south of the downtown; and the Campbell Center for Historic Preservation Studies located on the initial Shimer College campus at extreme southern edge of the town. Cultural enthusiasts must witness an ‘oil on canvas mural’ painted by the eminent painter Irene Bianucci at the Mount Carroll post office, watch a theatrical performance at the Timber Lake Playhouse, and tour the Raven’s Grin Inn - the only year-round haunted house in the region. Visitors can enjoy their stay at the Prairie Path Guest House, the Bridgewater Inn at the Historic Glenview, and the Inn at Molly’s.

From Quincy - Illinois’s “Gem City” to the enchanting river town of Fulton, the uncountable small towns in the nation’s 25th-largest and 6th-most populous state lure tourists with their distinctive allure. Each of these close-knit communities with its array of natural wonders, fascinating historical sites, distinctive cultures, quaint bed & breakfasts, world-class recreations, and warm hospitality offer memorable experiences for every vacationer. Pack your bags, and come and explore these towns with your loved ones on a fun-filled weekend trip.

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