Greenup is known as the “Village of the Porches”: overhanging porches line most buildings downtown. This distinctive feature of the town’s architecture leads to a discovery that extends throughout Cumberland County: here, you’ll encounter traces of transportation and local history, as well as protected woodland, a lake spanning several counties, and parks with a range of amenities.
Greenup’s history of roads, bridge, and depot
Greenup’s Main Street is also known as Cumberland St. and Illinois RT 121, and is part of the National Road. The connection between the street name and the historic route gives the town’s history a tangible point of reference. The Greenup Commercial Historic District is also part of this picture: it was added to the National Register of Historic Places in 1991.
West of Greenup, the Cumberland County Covered Bridge crosses the Embarras River on the old National Road. Dedicated in 2000, the bridge stands at the site of an original covered bridge from the 19th century. Two periods can be distinguished here: the earlier bridge at this location and the later dedication of today’s Cumberland County Covered Bridge. The historic depot recalls another aspect of local history: the era when railroads brought numerous freight shipments and travelers to Greenup.
The Cumberland County Historical and Genealogical Society preserves records to maintain the county’s local history. The Cumberland County Military Museum has a different focus: it honors veterans from Cumberland County who sacrificed their lives and livelihoods to defend their way of life. Together, these places of remembrance lead from historic records and transportation routes to an explicit tribute to veterans.
Woodland and Lake Mattoon
North of Montrose lies John Clyde Spitler Woods, an 18,865-acre natural area in Cumberland County. It protects high-quality dry-mesic and mesic woodland in the hills. Thus, alongside its historical themes, the county also offers a clearly defined natural area whose defining feature is the protection of these woodland habitats.
Lake Mattoon offers a different geographic perspective: the lake stretches across Coles, Cumberland, and Shelby counties. Lake Mattoon Marina is located at 1282 County Road 000 East, Neoga, Illinois 62447. This makes it easy to distinguish between the county’s two natural attractions: John Clyde Spitler Woods is a named protected area north of Montrose, while Lake Mattoon spans county boundaries.
Parks with a range of amenities
The parks can also be distinguished by their specific amenities. The details below can help you match a location’s offerings to your interests:
- Haughton Park in Greenup has two lighted baseball fields, two lighted tennis courts, a lighted basketball court, a picnic area, and playground equipment.
- Jennings Park in Neoga has three lighted tennis courts and two lighted baseball fields.
- Neal Park in Toledo has a baseball field, two lighted basketball courts, a lighted tennis court, horseshoe pits, playground equipment, and picnic areas.
- Homecoming Park in Jewett offers a shelter, playground equipment, four horseshoe pits, and a monument.
Amenities range from lighted sports fields and tennis courts to horseshoe pits, picnic areas, and a monument. If you plan to visit one of these parks, check its amenities before your visit; they may change.
An annual event in Greenup
The Cumberland County Fair is held annually in Greenup; its 137th edition is scheduled for 2026. If the fair is relevant to your travel plans, check the event dates in advance. Along with the history of roads and railroads, it adds a recurring event to the attractions, without requiring you to treat the county’s different places and themes as one and the same.
Discover more destinations: Greenup, Edgar, McDonough, Douglas County, Johnson County, Kane, Hancock County, Wayne County.
For the main travel overview: Illinois.
