Itinerary: A weekend trip to sites on Illinois’ Underground Railroad
With more than 50 sites on our map of Illinois’ Underground Railroad, it would be quite challenging to make the 1,100-mile round trip in a single vacation.
But as September is International Underground Railroad Month, if you’ve got a few days free, plan a weekender to visit the places where freedom seekers took refuge in their escapes from enslavement and get to know the stories of how they made new lives for themselves in Illinois communities.
This 3-day itinerary will require car travel and starts off in the Chicago area. It focuses on visiting as many sites within a reasonable time frame, with an emphasis on sites with interactive activities for an engaging trip.
Sites are all around the state, so if a trip isn’t feasible, be sure to take a look at our full map of Underground Railroad sites — there might be places to visit much closer to home than you think.
Friday
Your destination is Alton, in the southwest corner of the state near St. Louis. But you have a few options for the journey. You could stop at the southern edge of Chicago to visit the Jan and Aagje Ton Farm, the first site in the city to be named to the Underground Railroad Network to Freedom program.
It’s also part of the African American Heritage Water Trail, beginning at the Cook County Forest Preserves’ Beaubien Woods and ending in south suburban Robbins. The 7-mile Little Calumet River trail requires those taking to the water to be experienced paddlers or traveling with an experienced guide, but you can also enjoy the view from the shore.
By taking I-57 south through Champaign, you could make a stop in Oakland to see the Dr. Hiram Rutherford House. The abolitionist faced off against Abraham Lincoln in a case involving a family of freedom seekers. It’s only open until 2 p.m. Fridays, so this one is probably best for the early risers.
Or you can make a slightly shorter, 4 ½-hour drive via I-55 through Springfield. After strolling by the Old State Capitol, spend some time walking through history at the Lincoln Home National Historic Site. Among the places surrounding the Civil War-era president’s home are the Jameson Jenkins lot, the site where the home of Jenkins — believed to have used his transportation business to aid freedom seekers — once stood.
If you reach Alton later in the day, you can unwind in town, or cross the river into St. Louis for a night out. On the Illinois side, Alton has dozens of restaurants, a handful of craft breweries and coffee shops. For a stay that mirrors your sightseeing plans, there’s at least one Airbnb in a historic house, as well as a traditional bed-and-breakfast inn known as Beall Mansion.
Saturday
If you’ve timed your trip to include one of the third Saturdays of the month from September through November, the Freedom to Equality tour offers a convenient way to see many of Alton’s Underground Railroad sites and other places teeming with Black history. (If you miss the Sept. 16 tour, the next one will be Oct. 21.)
If the bus tour isn’t an option, you can explore the town yourself, or head north toward Jacksonville. On the way, the Hamilton Primary School will host a festival Sept. 23-24 that includes tours of the historic school and Underground Railroad stop, as well as a bake-off auction and a Sunday chicken dinner. On other dates, tours can be scheduled in advance.
If the weather is nice, your 1 ½-hour drive could detour 30 minutes over to the New Philadelphia National Historic Site, which became a national park at the end of 2022. The town named for brotherly love was the first in the U.S. founded and registered by a Black person, “Free” Frank McWorter.
Now, the nonprofit New Philadelphia Association manages a visitors’ kiosk and virtual tour. A free app enables visitors to view 3D representations of buildings overlaid at their original locations within the existing landscape.
Jacksonville is teeming with historic Underground Railroad sites, and most can be viewed on the Woodlawn Farm bus tours — the next one is Oct. 15. Woodlawn Farm itself has open tour days from 1-4 p.m. Saturdays and Sundays from May through September. The farm’s owners aided freedom seekers, employed them and built cabins on the property for free Black families.
The Jacksonville visitors bureau maps out a self-guided tour of its Underground Railroad sites, which include the Congregational Church at the heart of the town’s abolitionist movement.
If you’re staying overnight, bed-and-breakfast inns are housed in elegantly restored mansions, such as Blessings on State and Villa DeWolf. Those who enjoy a night under the stars have multiple options for camping. A few popular restaurants include The Little Stove, Proud Richard’s, Norma’s North Star Cafe and Leo’s Pizza.
Sunday
As you head to Chicago, you have a few options. Detour in Princeton to see the Owen Lovejoy Homestead, once home to the abolitionist minister and congressman, and brother of murdered abolitionist Elijah Lovejoy. It is said that Frederick Douglass stayed here, and docents in present day can point out a hidden area above the stairs where freedom seekers hid. Tours take place 1-4 p.m. Fridays through Sundays from May through September.
A shorter drive through Springfield and Bloomington on I-55 will pass by the I&M Canal Headquarters, open from 1-4 p.m. Wednesday through Sunday. Even before the I&M Canal was completed in 1848, freedom seekers would follow its path as they headed for Chicago, aided by abolitionists along the route.
Other routes could include visits to the African American Heritage Water Trail, if it wasn’t visited at the start of your trip; or through the west suburbs to visit Blanchard Hall, the 1846 Israel Blodgett House, the Sheldon Peck Homestead or Graue Mill and Museum, all stops on the Underground Railroad. As a bonus, this course of action could also include a visit to the Ten Mile Freedom House Marker — conveniently located in a McDonald’s parking lot for hungry travelers.
But if the weather is nice and you’re in the mood to stretch your legs after so much time in the car, spend the afternoon in Graceland Cemetery. Take in the final resting place of many Underground Railroad conductors, freedom seekers and abolitionists along the historic cemetery’s sweeping landscape. Self-guided audio tours describe the historic inhabitants, offering a final moment to reflect on the many lives shaping Illinois Underground Railroad before you head home.
