Wine Tasting in Freeport

Select Local Merchants

Travelers follow Jo Daviess County's sprawling fields and undulating hills toward Massbach Ridge Winery’s 18+ acre estate. Founded by the Harmston family in 2003, the winery’s proprietors select grapes grown in Jo Daviess County to concoct their batches of reds and whites. Members of the winery family escort guests on impromptu tours before rendezvousing in the tasting room or on the patio for samplings. The outdoor patio grants a heightened view of the vineyards below, which visitors can wander through on quests for vine-ripe copies of The Grapes of Wrath. In addition to its frequent tastings and tour sessions, Massbach Ridge Winery hosts a number of wine-related events each year.

8837 S Massbach Rd
Elizabeth,
IL
US

Situated inside a renovated historical building, Northleaf Winery pays tribute to the location’s agricultural past while bottling more than a dozen wines. Fragrant samples of peppery zinfandel and floral pinot grigio are poured at the wooden tasting bar, which hosts open tastings and private pairings of wine and artisanal chocolates or cheese. Next door, the bistro and market stocks a tempting selection of Wisconsin cheeses and party trays, along with fresh salads and build-your-own grilled sandwiches with included blueprints.

232 S Janesville St
Milton,
WI
US

Village Vintner Winery & Brewery poses a gastronomic triple threat, operating as not just a restaurant and winery, but also a fully functioning brewery. A battalion of stainless-steel machinery ferments the hand-selected wheat and barley that make up the vanilla-cream ale, the German-style hefeweizen, and the Vintner Hop Rocket, an 8.2% ABV varietal culminating from six types of hops and mad, mad science. At the tasting bar, guests can sample these brewery end products, along with Village Vintner’s expansive selection of homemade red, white, and fruit wines. The main restaurant area houses a wood-fired pizza oven, which bakes the pesto pizzas and smoldering baby back ribs that complement potables.

A spirit of good-natured fun permeates the copper-hued premises, as evidenced by a free monthly wine and mug club. Live music is a common occurrence on Friday nights, and Wednesdays star Chef Rob’s pork special.

2380 Esplanade Dr
Algonquin,
IL
US

Artalé edifies eager palates with a Herculean selection of classy beverages and elegant edibles. The epic selection of bottled marvels includes a variety of imports, specialty imbibitions, and wines, such as the Avignonesi Vino Nobile Di Montepulciano 2007, whose black-cherry fruitiness and spice earned it a rank of 83 from Wine Spectator ($29.99/bottle). A bevy of bruschettas, nuts, chocolates, and cheeses serve as a solid foundation for other intoxicating distillations, from the Elk Cove pinot gris 2009, which follows notes of pear, apple, and lime with a almond-petal finish ($16.99/bottle), to the Castello d'Albola chianti classico 2007, a miracle of dark cherry with a floral kiss ($14.99/bottle). An army of 400 craft and microbrew beers flank this cork-crowned armada, and a selection of top-shelf liquors brings up the rear. Artalé's bottle-lined stronghold frequently hosts tastings to exhibit cheese-and-wine-pairing techniques, seasonal drink selections, and the latest oenological lingo, with terms including "woody" and "purple-ish."

6876 Spring Creek Rd
Rockford,
IL
US

Dozens of local products and cheeses populate the comfortable confines at the Wisconsin Cheese & Wine Chalet, where a knowledgeable staff greets guests with friendly grace. Catch the breeze on the outdoor patio, or sample from the wine selection as the team prepares its signature Wisconsin Cheese & Sausage 18-inch tray, a massive mound of meats and cheese perfect for sating starving Labor Day revelers. The platter arrives stacked with one pound each of mild cheddar, colby jack, and pepper jack cheeses from the Wisconsin Cheese Company. The array of summer sausages includes 12 tasty ounces of the Wisconsin Sausage Company's original, garlic, and cranberry summer sausages, each crafted from 100% Angus beef.

11190 N Goede Rd
Edgerton,
WI
US

To winemaker Alwyn Fitzgerald, The Fisher King isn't just a medieval legend; he represents a way of life. According to Arthurian myth, as the wounded Fisher King grew stronger in the spring and into the summer, so did the surrounding land and harvest. Inspired by this relationship between man and Earth, Alwyn founded Fisher King Winery in spite of the Midwest's temperamental climate. There, he hand-processes the local, cold-hardy grapes that give his small-batch wines a light yet complex flavor profile. His decision to use mostly Midwestern grapes in his winemaking process has certainly paid off: his Blue Rapture white wine won a gold medal at the U.S. National Wine Competition, as well as a Best of Class and double-gold award at the International Eastern Wine Competition in 2013.

Outside of Fisher King Winery, a hanging sign with gold letters depicts the company's mythological namesake. Inside, large windows provide a glimpse of the tanks and pipes in the production area, where Alwyn and his family produce their award-winning Blue Rapture wine, alongside other dry-to-sweet red and white varietals. The tasting room's hardwood bar and tables give visitors a place to sip popular wines by the flight, glass, or bottle, and nibble on local artisan cheeses. Fisher King Winery also hosts regular live performances from local and regional musicians.

102 W Main St
Mount Horeb,
WI
US