The First Hundred Miles Fall Wine Trail

Six Can’t-Miss Wine Bars and Wineries along Route 66

Experience the viticulture of Route 66, by planning a fall road trip with your friends to six of the best wine bars and wineries The First Hundred Miles has to offer the amateur sommelier. From Joliet to Pontiac, you’ll be surprised at all the hidden gems you find during your wine sampling excursion.

Bishops Hill

310 Bridge St., Joliet

Once the headquarters for the Joliet Catholic Diocese, and before that the estate of a German brewmaster, this striking limestone castle is now hosting wine tastings and other special events. During extensive restorations, much of the original on-site brewery was discovered and painstakingly restored with reclaimed materials. The grotto-like structure houses the Bishops Hill processing equipment, tanks and barrel-aging rooms. To reserve your own private tasting, and to see a list of upcoming events, visit

The Wine Cafe

130 Bridge St., Wilmington

Conveniently located on historic Route 66, and just 10 minutes off I-55, Wilmington’s Wine Cafe offers an assortment of wine and beer from local and other Illinois wineries/breweries, freshly brewed coffee and slot machines associated with large chain casinos. The Wine Cafe specializes in public tastings, private parties and live music. Be sure to follow The Wine Cafe on Facebook to see all of the upcoming tastings and events.

HopScotch & Vine

24047 W. Lockport St., Plainfield

Located in the heart of downtown Plainfield, HopScotch & Vine offers delectable breakfast, lunch and dinner – including a curated menu of wine, beer and craft cocktail options. The cozy, upscale restaurant showcases a broad New American menu, featuring favorite items like Chicken Piccata, Walnut Sage Pesto Penne and Bruschetta Flatbread. As the name implies, you’ll also discover an artfully selected array of wines designed to pair with the tasty entrees and appetizers.

Wine and Cheese Company

24104 W. Lockport St., Plainfield


You’ll come for the wine and cheese, but that’s not all they’re serving up here at Wine and Cheese Company in historic downtown Plainfield. There’s so much more to savor from specialty brewed beers to small plates and charcuteries, salads, quiche and sweet treats. Excellent wines by the bottle or glass include a nice selection of both domestic and imported choices. Add a stop at Wine and Cheese Company to your day of antiquing or bridal shopping, and you’ll be glad you did. Enjoy both indoor and outdoor (Fido friendly) seating, weather permitting.

PK UnKorked Wine Shop and Tasting Room

826 N. Ladd St., Pontiac

Cap your trip along The First Hundred Miles with a decadent glass of wine at Pontiac’s own PK UnKorked. Home to over 100 varietals of vino, this chic tasting room and shop is the perfect place to enjoy a glass, flight or bottle with your road trip companions. In the store, you’ll find novelty wine items, decor and kitchen accessories, along with the occasional free live musical performance. Be sure to grab a bottle of Route 66 Special Label, a wine that makes a great Mother Road souvenir.

Take 5 Rendezvous Wine Bar

310 S. Third St., Fairbury

Located just beyond The First Hundred Miles, Fairbury’s Take 5 Rendezvous Wine Bar is a hidden gem destination, open to the public on select days, and available to reserve for your private group events. Functions can be arranged inside or on the property’s spacious lawn (you’ll find the wine bar inside the historic Hoffman House B&B). Their upcoming Sip-n-Shop event, planned Nov. 4 and 5, will feature many local vendors throughout Hoffman House, which will be fully decorated for the holidays. That weekend, Take 5 Rendezvous will serve wine, beer and hot apple cider from 5 to 9 p.m. Friday, and 9 a.m. to 1 p.m. Saturday (which will include mimosas and bloody marys).