Happy Trails
By Naperville Magazine
May 2025 View more Featured
By Jeff Banowetz
Looking for a different kind of getaway? Tourism trails offer visitors a way to dive into a region’s specialty—be it food, drink, music, or culture—and craft a vacation that helps you discover something new. These four trails are worth exploring.
1. The Kentucky Bourbon Trail
A trip to the Bluegrass State around Lexington offers beautiful scenery, fine dining, and a chance to learn more about—and, of course, taste—the best offerings in the birthplace of bourbon.
When the Kentucky Bourbon Trail was first organized in 1999, it brought together seven distilleries across the state. A quarter century later, it now boasts more than 60 distilleries and tasting rooms, highlighting the huge jump in popularity for Kentucky’s most famous export. “So much has changed in the last 25 years,” says Amandalin Ryan, director of the Kentucky Bourbon Trail Experience. “Back then, you would show up and maybe somebody would walk you around. Now you can take a cocktail class or learn about the history and production styles of different kinds of bourbon. You’ll eat amazing food, and there’s so many more things to do as part of the experience. It’s become a real destination now.”
The trail itself stretches across the entire state, so it makes sense to focus your attention on one of the six regions. The Lexington area is a great starting point, particularly for those who are interested in more than just bourbon. Located in the heart of horse country about a six-hour drive from Naperville, Lexington is a college town (Go UK Wildcats!) that features excellent dining options, pretty scenery, horse racing, history, and a calendar packed with events. Whether you like your bourbon straight or in a mint julep, you’ll find lots to love here.
ON THE TRAIL
You don’t have to spend much time in Kentucky to hear the oft-quoted phrase, “All bourbon is whiskey, but not all whiskey is bourbon.” Bourbon is a barrel-aged spirit made primarily from corn, and while you can distill it outside of Kentucky, more than 95 percent of it is produced in the state. (It does, however, need to be distilled in the United States, per a 1964 resolution by Congress.) The distilling process dates back to the late 18th century, just after the American Revolution, when European immigrants brought their knowledge of distilling whiskey (typically made with other grains) to the state.
While the origins of the name “bourbon” are a bit murky—Bourbon County, Kentucky, and Bourbon Street in New Orleans both claim credit, and there are several other theories—all agree that the product developed in Kentucky. To create bourbon, distillers must follow very specific steps: It must be aged in new, charred-oak containers; it cannot be distilled above 160 proof; and no color, flavoring agents, or other spirits may be added. Part of the joy in the Kentucky Bourbon Trail is discovering how distilleries are able to create very different products using quite similar procedures. “You can cater your experience to what you like to drink, but you’ll always find something new,” Ryan says.
Close to Lexington, you may want to start at Woodford Reserve Distillery, a National Historic Landmark that dates back to 1812. “It’s a beautiful place with lots of old stone buildings,” Ryan says. “And you can pair it with a visit to Castle & Key just down the street.” Castle & Key opened in 2014, but it’s a restoration of the previous Old Taylor Distillery, which dates back to 1887. The restored castle on the property looks as if it was plucked out of medieval Europe, and it also features an impressive garden and the longest aging warehouse of its kind anywhere. Town Branch, located in Lexington, is the only “brewstillery” on the trail. In addition to bourbon, it also makes beer, offering another tasting option. If you love both, try its Kentucky Bourbon Barrel Ale, which combines flavors of each.
You’ll find 18 distilleries within 30 miles of Lexington, and if you don’t have a designated driver, a tour company is a good option: a local expert can help you plan a trip and take care of all the transportation.
SIDE TRIPS
When in horse country, take advantage of it. While the Kentucky Derby at Louisville’s Churchill Downs gets the most attention, live racing is open during its Spring Meets in May and June. (Two additional sessions occur in September and November.) In Lexington, Keeneland Race Course has been holding races in April and October since 1936. The beautiful track is worth a visit even without racing. It’s open to the public every day for tours, where you can watch morning workouts or the horse auctions.
The Kentucky Horse Park, located in Lexington on 1,200 acres of bluegrass farmland, offers a variety of ways to learn more about horses. You’ll find three museums, plus daily presentations showcasing breeds, horse-drawn tours and carriage rides, and special exhibits. It also hosts more equine competitions than any venue in the country, including steeplechase, cross-country, dressage, and rodeos. There are more than 450 horse farms in the bluegrass region, and many offer tours.
WHERE TO STAY
Enjoy a stay in horse country at The Campbell House, an historic boutique hotel located just outside downtown Lexington. It melds iconic horse farm fencing and architecture with modern style for a memorable getaway. Its Rackhouse Tavern also features an extensive bourbon list.
MORE INFO
For the complete list of distilleries on the Kentucky Bourbon Trail, visit kybourbontrail.com. For more information on Lexington, including experiences and tour operators, see visitlex.com.
2. The Crooked Road Heritage Music Trail
Country, bluegrass, and other forms of “heritage” music have deep roots in southwestern Virginia. This trail offers a chance to listen in one of the country’s most beautiful settings.
Many regions of the country are known for music, but few outside of southwest Virginia would probably recognize this area as one of them. So while you may not have heard of The Crooked Road Heritage Music Trail, you’ll be familiar with the many styles of music that can trace its roots here.
“It’s a 330-mile-long driving trail throughout the mountains of southwest Virginia that connects 10 major anchor points and 60 affiliated venues that are cultural institutions connected to the region’s legacy of traditional, bluegrass, old-time, and early country music,” says Tyler Hughes, executive director of the trail. The path basically follows historic Route 58 through Virginia near the North Carolina border, with several spurs that follow deeper into the mountains.
As for the name? “As anyone who’s ever driven here can tell you, the roads are very curvy,” Hughes says. “You need to pay attention driving in the mountains.”
For lovers of heritage music, a trip here offers a celebration of its history with numerous small venues featuring an abundance of old-time string bands, gospel, blues, bluegrass, and country music. They’ll also find an inviting—and still relatively undiscovered—natural setting with lots of outdoor adventures to fill the days.
ON THE TRAIL
Traditional American Heritage music developed in the Appalachian Mountains when immigrants from Europe brought their fiddle tunes and ballads to the region. It would be infused with elements of West African music, which introduced the banjo, and continued to develop through the 19th century, evolving into country music and all its iterations by the early 20th century.
Some of the highlights of the trail include the Carter Family Fold in Hiltons, which pays homage to the first family of country music and has live performances every Saturday night. “It’s a great place for visitors to really experience how immersive the Crooked Road experience is,” Hughes says. “Everyone’s just welcome to jump up on the dance floor, and there’s always someone willing to teach you.” The Floyd Country Store in Floyd has become a renowned community gathering place, with a traditional Friday night jamboree for more than 40 years. “It draws music lovers from around the world to the quaint general store with authentic old-time and bluegrass performances and local jam sessions spilling out into the streets,” Hughes says. “You really get a taste of that history and the connection to the local community and local culture.” The Blue Ridge Music Center, located on the Blue Ridge Parkway in Galax, offers hundreds of performances from May through October at its outdoor amphitheater. It also features an indoor theater and museum. Its “Roots of American Music” concert series is held on Saturday evenings through the summer. The Ralph Stanley Museum in Clintwood chronicles the career of the legendary bluegrass performer and features a large collection of memorabilia in a four-story Victorian home. In Bristol, Virginia, just across the border from its sister city Bristol, Tennessee, the Birthplace of Country Music is a museum affiliated with the Smithsonian Institute. It highlights the role that the 1927 Bristol Sessions played in the creation of country music.
SIDE TRIPS
While you’ll have to do some driving to hit all the highlights of the trail, Abingdon serves as an excellent basecamp. The small mountain town is home to several attractions that have made it one of the top destinations in the region. The Virginia Creeper Trail is a spectacular rail-to-trail that’s very popular among cyclists and hikers. Unfortunately because of damage from Hurricane Helen last fall, 18 miles of the 34-mile route are still closed. The Appalachian Trail also runs through this region for more serious hikers who don’t mind elevation gains. You’ll be rewarded with spectacular views, but again, check for updates before heading out as damage remains from the storm and sections of the trail may be closed through this summer.
You don’t have to worry about the Barter Theatre, which has been a mainstay in Abingdon since 1933, when in the midst of the Depression, it offered admission for 35 cents “or the equivalent amount of produce.” You’ll find Broadway musicals and dramatic performances throughout the year in this historic building that dates back to 1876.
WHERE TO STAY
The Martha Washington Inn & Spa in Abingdon is an attraction of its own. The inn began as a private home in 1832 before it became the Martha Washington College, which was one of the first schools in the country to offer higher education for women. The college was closed in 1932 and became an inn, keeping the same name. It’s now renowned for its blend of charming history and modern amenities, with 63 uniquely designed rooms.
MORE INFO
Find out more about The Crooked Road Trail at thecrookedroadva.com and visitabingdonvirginia.com.
3. Madison on Tap Craft Beverage Trail
Craft beer and spirits in Wisconsin? Perhaps that’s not much of a surprise. But the capital city of the Dairy State has tons of summer activities to make it the perfect spot for bar-hopping fun.
Madison, Wisconsin, has a lot going for it. It’s a college town, with nearly 50,000 students from the University of Wisconsin bringing energy and excitement to the area. It’s the state capital and second-most-populous city in Wisconsin. It’s surrounded by lakes for fun on the water, and it’s one of the country’s best cities for cycling. Throw all those together, is it any surprise that it’s also home to one of the most thriving craft-beer scenes in the Midwest?
“As a state, we’re of course known for our breweries and distilleries,” says Sarah Warner, communications manager for Destination Madison, the tourist organization that helped create the Craft Beverage Trail. “In Madison there are more than 30 breweries and distilleries to explore, so that really inspired our team to create a trail that helps both visitors and locals discover all that’s available to them.”
Of course, man does not live on beer alone, so it also helps that Madison has become one of the top food destinations in the state, with the largest producer-only farmers’ market in the country and more than 40 James Beard Awards in the last 25 years. While it has long been a proponent of farm-to-table restaurants, that local, sustainable, and creative mantra has influenced craft brewers and distillers as well.
At just over a two-hour drive from Naperville, Madison is close enough for a quick weekend escape, with enough activities to keep you wanting more. It’s also small enough that beer lovers can stay downtown and find plenty of places to sample without having to drive.
ON THE TRAIL
Start with Madison on Tap, a free service (no app needed) that provides information directly to your phone. The mobile pass provides a curated list of breweries, cideries, and distilleries in addition to deals at each. You also can check in at spots along the trail to earn points toward rewards (top prize is a weekend stay and private tour).
The tap room at Giant Jones Brewing Company is a great place to start if you’re staying downtown. This women-owned, certified organic craft brewery (931 E. Main St.) is known for its “big beers for everyone,” with strong flavors. It typically offers a selection of more than three dozen styles made onsite, ranging from American ales to more international offerings, like its British-Style Barleywine. Working Draft Brewery (1129 E. Wilson St.) is known for its hoppy lagers and European ales. The art-filled space was created in 2018, and its flagship creations are a Czech-style pale lager (To Those Who Wait) and a hazy IPA (Pulp Culture). Stark Weather Brewing (2439 Atwood Ave.) offers a rotating selection of seasonal offerings from hoppy IPAs to rich stouts—plus a chef-curated menu of better-than-typical bar food, including award-winning chicken wings. For cider, Hidden Cave Cidery (in nearby Middleton, Wisconsin) has a dog-friendly tasting room and patio.
If you gravitate toward spirits, make sure to stop by State Line Distillery (1413 Northern Court), Madison’s first “grains to glass” distillery. It uses locally sourced grain to create spirits onsite and then adds fresh ingredients to make unique craft cocktails. Put the experienced mixologists to the test with this one-of-a-kind Madison bar.
SIDE TRIPS
If you’re in town on a Saturday, take a trip to the Dane County Farmers’ Market on the Square, held around the Capitol from 6:15 a.m. to 1:45 p.m. You’ll find a wide collection of vegetables, meats, cheeses, flowers, and specialty products from more than 130 Wisconsin vendors.
Madison loves its lakes, and the summer is the perfect time to get the most out of them. “We like to call it urban outdoor adventure,” Warner says. “If you’re staying downtown, you can walk 10 minutes and hop in a kayak. Go out on the water, come back, and pick a bike rental. We have great biking and walking trails all within the downtown area.”
At Brittingham Boats in Brittingham Park, you can rent kayaks, canoes, standup paddleboards, and fishing boats to enjoy Lake Monona, with excellent views of the city’s skyline and the Capitol. Madison is one of only five Platinum-Level Bike-Friendly Communities in the country, so take advantage of the area’s trails by using Madison By Bike, which will help you plan routes around the city and beyond.
WHERE TO STAY
The recently opened Saddlery (327 E. Wilson St.) offers both short- and long-term rentals in a historic brick building downtown. You’ll find state-of-the-art conveniences with loft-style living areas.
MORE INFO
For more to do around the state’s capital city, see visitmadison.com.
4. Lake Michigan Shores Wine Trail
Southwest Michigan’s beaches always have been a big draw, but the area has developed a strong community of wineries that offer more reasons to visit.
Countless Chicago-area families have been vacationing in southwest Michigan for years, and they probably never knew they were in one of the country’s top viticulture areas. Yes, this favorite vacation spot is also one of the best places for growing grapes.
While there are a number of essential factors for cultivating grapes—including soil conditions and yearly rainfall—you can thank Lake Michigan for helping to create the perfect microclimate for a vineyard. “Ninety percent of Michigan’s vineyards are in this corner of the state,” says Claire Kliss, executive director of the Lake Michigan Shores Wine Trail. “It’s really where we are in relation to Lake Michigan that makes it possible. It’s a moderating influence. In the spring, the lake is cold, which keeps things from budding too early. And in the fall, it’s warm enough to extend the growing season, and we can keep the grapes on the vine a little bit longer before harvest.”
The trail was founded in the early 2000s by one of the area’s wine pioneers, David Braganini, whose family had been producing wine in the region since the 1930s with St. Julian’s Winery. “He said, ‘We really need to get the word out that there are wineries out here,’ ” Kliss explains. The trail has now grown to 15 members, and the southwest Michigan wine scene has matured in the last two decades, with more tasting opportunities, winery tours, and support infrastructure. “There’s so much that can be grown here,” Kliss says. “Each winery has their own personality. Each winery offers a different flavor. You really have a lot to explore.”
ON THE TRAIL
Kliss also works for Contessa Wine Cellars in Coloma for third-generation winemaker Tony Peterson. “We have a really good Pinot Grigio, but what I like to tell people is that we have something for everyone,” Kliss says. “So we have drys, but we also have some sweets for those people that like to indulge in a sweet wine. Everyone has a different palette, and I think it’s important to honor that.” Its tasting room resembles an Italian villa with its terrace overlooking the vineyard.
12 Corners Vineyards is an estate winery in Benton Harbor with additional tasting rooms in South Haven and Grand Haven. You’ll find Riesling, Cabernet Franc, Merlot, Chardonnay, and Traminette among its many varieties. St. Julian Winery in Paw Paw is still owned by the Braganini family, and it’s Michigan’s oldest and most award-winning winery. Take an enhanced tour, which includes viewing the full production facility, learning about the wine-making process, and a tasting. White Pine Winery’s tasting room in St. Joseph specializes in “aromatic whites like Riesling and Pinot Gris and fruit-driven reds like Syrah and Merlot.” The grapes are grown at a variety of local vineyards nearby.
SIDE TRIPS
Lake Michigan may be great for the production of grapes, but it’s also the region’s top attraction during the summer. Enjoy the beaches in Benton Harbor, St. Joseph, and South Haven, just to name a few. Warren Dunes State Park features three miles of sandy shoreline and dunes that rise up to 260 feet for the adventurous.
Tackle another dune experience farther north with the Saugatuck Dune Rides. A driver will take you on a 40-minute tour of the dunes in a thrilling ride. While in the Saugatuck area, visit what’s known as Michigan’s Art Coast. Downtown Saugatuck in particular is filled with galleries, boutiques, and shops for a day of relaxing retail therapy.
Cyclists will enjoy the Kal-Haven Trail, a 34-mile crushed limestone trail that connects South Haven to Kalamazoo. The early miles out of South Haven along the Black River are tree-covered and spectacular.
WHERE TO STAY
South Haven has spectacular beaches, a historic lighthouse, and an easily walkable downtown filled with restaurants and shopping. The Carriage House at the Harbor is a popular bed and breakfast—and within walking distance of everything. Each of the 12 guest rooms are well furnished, and you’ll certainly enjoy the view of the harbor from the deck.
MORE INFO
For more information on the Lake Michigan Shores Wine Trail, visit miwinetrail.com.
Photos: Keeneland; Kentucky Distillers Association (drink, castle & key, Woodford Reserve); Sydney Char (horse farm); John Snell (Keeneland); Virginia Tourism (musicians); Rick Hamm (Barter Theatre); The Martha; benedek/istock (Capitol); Madison Craft Brew Trail (beer); Sharon Vanorny/courtesy of Destination Madison (boats); csfotoimages/istock (farmers’ market); Visit South Haven; Lake Michigan Shore Wine Trail (trail and tasting); Pure Michigan (lighthouse)
