🌿 RelaxedWeekend · from St. Louis, MO
The Shawnee Hills Wine Trail & Rend Lake — Southern Illinois Unwound
Southeast across the Mississippi, the flat prairie gives way to the wooded ridges of the Shawnee Hills, home to Illinois' first designated wine region and its most beautiful wine trail. Day one settles into the Shawnee Hills Wine Trail, tasting at the pioneering estates of Blue Sky and Alto Vineyards amid the oak-covered hills that give the region its cool-microclimate character. Day two shifts to water: Rend Lake, an 18,900-acre reservoir ringed by the Wayne Fitzgerrell State Recreation Area, where lakeside trails, a resort golf course, and the little village of Whittington make for an easy morning before the drive home. Overnight is at the Rend Lake Resort, right on the water. It's a relaxed two days of vineyards and lakeshore, all within a comfortable drive of the city.
Day 1 — The Shawnee Hills Wine Trail: Blue Sky & Alto VineyardsDay 2 — Rend Lake, Wayne Fitzgerrell State Recreation Area & Whittington
Day 1 — Shawnee Hills Wine Trail, IL
Day 1 — Shawnee Hills Wine Trail, IL
🚗 2 hr 55 min driving📍 4 stops
🌅
Morning
🚗
Drive
St. Louis, MO → Shawnee Hills Wine Trail, IL
2 hr 10 min8:00 AM → 10:10 AM
Alto Vineyards
★ 4.7Alto Vineyards, founded in 1988 near the village of Alto Pass, was one of the pioneers that launched southern Illinois' modern wine industry and helped establish the Shawnee Hills as the state's first American Viticultural Area in 2006. Set against the wooded ridges of the Shawnee National Forest, its tasting room pours a wide range built around hardy French-American hybrids — Chambourcin, Vignoles, Traminette, and the popular sweet blends that put the trail on the map. It's a fitting first stop: the family behind Alto is widely credited with proving that the cool, elevated Shawnee Hills microclimate could grow serious wine. The shaded grounds are made for a relaxed morning flight.
10:10 AM📍 See location
🍽️
Lunch
Blue Sky Vineyard
★ 4.6Built to evoke a Tuscan villa, Blue Sky Vineyard is the showpiece of the Shawnee Hills trail — a handsome stone-and-timber estate with a bell tower, a wide terrace, and vineyard rows rolling down toward the forested hills. Beyond a broad list of estate wines, Blue Sky runs a full kitchen, making it the natural midday meal of the day: wood-fired flatbreads, panini, and cheese and charcuterie boards served on the terrace with a glass of Chambourcin or Vignoles. Live music often plays on weekend afternoons. It's the kind of place designed for lingering, and there's no reason to rush lunch here.
11:10 AM📍 See location
☀️
Afternoon
Von Jakob Vineyard & the Shawnee Ridges
★ 4Round out the wine-trail afternoon at Von Jakob, a hilltop estate that pairs a well-regarded winery with a small brewery and sweeping views over the surrounding Shawnee ridges. The wraparound decks look out across vineyard and forest toward the highest hills in the region, and it's a fine place to slow down with a final tasting as the light softens. Von Jakob also keeps a few animals and gardens on the grounds that make it a relaxed spot to wander. From here it's a short drive down to Rend Lake for the night — an easy transition from the hills to the water.
12:10 PM📍 See location
🌙
Evening
🚗
Drive
Shawnee Hills Wine Trail, IL → Rend Lake Resort, Whittington, IL
45 min5:00 PM → 5:45 PM
🛏️
Rend Lake Resort
The Rend Lake Resort sits directly on the water at Whittington, offering lakeside lodge rooms and freestanding boat-dock cottages built out over the lake — some of the only accommodations in Illinois where you can step from your room onto a dock. The resort has its own restaurant with lake views, so dinner requires no further driving, and the setting is quiet and unhurried once the day boaters have gone. Book a boathouse unit if available for the full waterside effect. For travelers who prefer conventional lodging, the nearby towns of Benton and Mount Vernon have standard chain hotels a short drive away.
Day 2 — Rend Lake, IL
Day 2 — Rend Lake, IL
🚗 2 hr 15 min driving📍 3 stops
🌅
Morning
🚗
Drive
Rend Lake Resort, Whittington, IL → Wayne Fitzgerrell State Recreation Area, IL
5 min8:00 AM → 8:05 AM
Wayne Fitzgerrell State Recreation Area
★ 4.5This 3,300-acre recreation area occupies a long peninsula reaching into Rend Lake, the second-largest man-made lake in Illinois at nearly 19,000 acres. The morning is for the water: easy shoreline trails, quiet coves for wildlife watching, and one of the finest bird-watching areas in the state — the lake is a major stopover on the Mississippi Flyway, and bald eagles, herons, pelicans, and huge flocks of migrating waterfowl are common seasonal sights. Boat and pontoon rentals are available at the marina for those who want to get out on the water. It's a peaceful, spread-out place, and even at its busiest the peninsula rarely feels crowded.
8:05 AM📍 See location
🍽️
Lunch
🍽️ Lunch9:05 AM
🍽️
Windows Restaurant at Rend Lake
The resort's lakeside dining room, with its wall of windows overlooking Rend Lake, is the obvious and best choice for a relaxed midday meal. The kitchen leans on regional American fare — fried catfish and other lake-country staples alongside sandwiches and salads — and the view of the water does the rest of the work. Grab a window table and take your time; there's nothing hurried about lunch here, and it's a pleasant place to regroup before the afternoon and the drive back.
2 options · tap to switch
☀️
Afternoon
Whittington & the Rend Lake Dam West Recreation Area
Before turning north, spend the afternoon around the tiny village of Whittington and the lake's western shore. The Dam West Recreation Area, at the foot of the Rend Lake dam, has a swimming beach, picnic groves, and long paved bike paths that trace the shoreline — an easy, flat way to stretch out a final walk or ride by the water. Nearby, a cluster of craft and antique shops and the seasonal artisan market give the area a low-key browsing stop. It's a gentle way to wind down the trip, letting the day cool before the two-hour drive back to St. Louis.
12:00 PM📍 See location
🌙
Evening
🚗
Drive
Rend Lake, IL → St. Louis, MO
2 hr 10 min5:00 PM → 7:10 PM
Plan your own escapeExplore more trips →