The Indiana Wine Trail is part of the country’s oldest and largest designated wine region, and the portion near Madison links the area’s six wineries. Start the 110-mile tour at Lanthier Winery (Madison’s oldest) with a glass of their most popular wine—the sweet, grapey Mill Street red. Loop around to Stream Cliff Farm Winery and Tearoom to grab a table in their outdoor gardens for a lunch featuring their fresh-grown herbs, like the dill and rosemary chicken salad. Finish up at the Ridge Winery tasting room for their award-winning blackberry-apple fruit wine, BlackJack. If you find you’ve sampled a bit too much vino, there are plenty of quaint bed-and-breakfasts nearby, many of which offer lush (pun intended) discounts for wine trail followers.
indianawinetrail.com, (800) 559-2956 for Madison-area trail