How to Travel the Trail, Part One: The Northern Experience

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When you're planning to travel the Indiana Uplands Wine Trail (or any wine trail for that matter) it's best to go in with a solid strategy: map out the locations of the wineries, estimate how much time you expect to spend at each, and set out to explore the towns you'll be visiting along the way. One of the unique aspects of the Indiana Uplands Wine Trail is that it exists entirely within an American Viticultural Area, or AVA, called the Indiana Uplands. This geographical, wine-growing region spans 4,800 square miles- that's a lot of ground to cover! Within the rolling hills and long, country roads which connect the 9 wineries of the Indiana Uplands Wine Trail, there are many places to stop, delight in local art and food, and retreat.

Planning your trip along the trail may include a whole host of experiences in addition to tasting the world-class wines that are produced in our Indiana AVA. In an effort to help you make a plan for your trail travels, we have put together some of our recommended places to stop along the way. From the northernmost winery on the trail, Oliver Winery, to the southernmost, Best Vineyards Winery, you'll have over 100 miles to trek (hopefully with your windows down) and enjoy the ride. Because it's an expansive trail with so much to see along the way, we recommend breaking your travel plans up into two halves: a northern trip and a southern trip. You can spend one weekend experiencing the northern part of the wine trail (Oliver Winery, Owen Valley Winery, Butler Winery, and Brown County Winery) and another entire weekend enjoying the southern part of the wine trail (French Lick Winery, Winzerwald Winery, Huber's Winery, Turtle Run Winery, and Best Vineyards Winery). 

The northern part of our trail is made up of the quintessential Indiana towns of Spencer, Bloomington, and Nashville. The group of us in the northern half of the trail got together to recommend some of our favorite spots  Here are some recommendations we hope will enhance your weekend in the northern half of the Indiana Uplands Wine Trail:


-Ponder the eclectic items at The Dragonfly Gallery gift shop on the square in Spencer. Seasonal items and timeless pieces can be found here in the restored Odd Fellows Meeting Hall. Learn how this little shop is helping to restore the vibrancy of this one-of-a-kind Indiana town!

-Delight in the quaint shops in the Village of Nashville. Unique hand-made items from local artisans abound in this little heart of Brown County. You will not leave empty-handed!

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-Enjoy the spice of life at Jit's Thai Bistro in Spencer. This small, family-owned Thai spot serves up daily lunch and dinner specials with a homemade touch. Try their pineapple fried rice if you're a fan of the sweet & savory combination of flavors!

-Step into the upbeat scene of downtown Bloomington at Malibu Grill. This laid-back, yet stylish, restaurant serves up healthy portions of steak, seafood, and a little bit of everything in-between. Sit on their front porch and enjoy the sights and sounds of this friendly college town.

-Indulge in historically-proven frozen treats at The Chocolate Moose in Brown County. This local company has been serving up their homemade flavors since 1933!

Photo from the Chocolate Moose- Brown County Facebook Page

-Craft the perfect night out at Big Woods Brewery: creative pub fare, delicious local beer, and toe-tapping live entertainment! Go for dinner or for an afternoon brew in cozy Nashville.

-Savor the funky atmosphere and fresh, elevated dishes at Uptown Cafe on Kirkwood Avenue in Bloomington. Breakfast, brunch, lunch, dinner- check this one off your list as soon as you get the chance.

Photo from the Michael's Uptown Cafe Facebook Page


-Re-energize at 5-star Main Street Coffee in the heart of Spencer. They serve small lunch bites and baked goods along with their rich, hot coffee and espresso drinks. Enjoy the charming, historic setting and friendly service, too.

-Take a "farm-to-fifth" tour at Gnawbone's Bear Wallow Distillery and taste their Indiana spirits! Feel pride in supporting this woman-owned, family-operated business and saying "cheers" to their Indiana traditions.

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-Enjoy craft beer at Upland Brewing's Brewpub and Wood Shop in Bloomington. Sample their variety of beers in a flight from their 12 rotating taps. Take a tour at the Wood Shop and learn how sour beers and produced. Some of their sours even use grapes from the Indiana Uplands to develop distinctly local fruit flavors!

Photo from The Upland Brewing Company Facebook Page

-Stop in at Cardinal Spirits for yet another taste of the Bloomington craft scene. Vodka, Gin, Liqueur, and more!


-Retreat in the hills, in style. Brown County Log Cabins has a place for you and your friends (or your entire family) for the weekend. Find a cabin with a hot tub for those chilly Indiana evenings or a cabin with a game room to keep the while family occupied!

-Explore Indiana's oldest state park, McCormick's Creek State Park, when you stay at the Canyon Inn in Spencer. With so much scenery and nature to take in, you might just need to stay two nights.

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-Make yourself at home at the Grant Street Inn in Bloomington. This cozy inn, made up of 5 unique buildings, has a variety of rooms to match your personality. Some showcase an old-world feel, while others have all the modern comforts for the urban traveler.


-Appreciate the wonderful, local artwork and historical collections at the Brown County Art Gallery. Rotating exhibits and events mean the gallery will never look the same twice!

-Uncover rare books, manuscripts, and special collections at the Lilly Library on the Indiana University Campus. This library welcomes scholars from around the world to visit its unique exhibits and delve into its rare collections.

-Become one with the Indiana Uplands in the hidden Green's Bluff Nature Preserve. Enjoy the quiet, rolling of the hills and the cool water of Raccoon Creek. The trails are full of unusual plants, steep cliffs, and one of Indiana's longest caves: Boone's Cave. Experienced hikers rejoice in finding this hidden gem!

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-Tour the T.C. Steele State Historic Site in Brown County. Honor the artistic tradition that began in this area in 1907 when Theodore Clement Steele made his home in Brown County.

-Revive your youthful curiosity at WonderLab Museum of Science, Health, and Technology in Bloomington. This is a must for those traveling with kids- play, learn, experiment, and create at this one-of-a-kind museum.


Traveling the Indiana Uplands Wine Trail is your adventure! We hope these suggestions help you make your journey through Indiana's Wine Country worth not only remembering but worth recreating frequently. Travel the trail for the best Indiana wine experiences and so much more! Keep your eyes out for part two of this how-to series for ideas of places to visit when you travel the southern portion of the AVA. See you soon!


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