Gay Summer Getaway: Madison, Indiana

Summer in Madison, Indiana, is nothing short of magical. Nestled along the Ohio River and surrounded by rolling Southern Indiana hills, this picturesque town is bursting with small-town charm, rich history, and endless things to do under the sun. With 133 blocks of preserved 19th-century architecture, Madison is the largest contiguous National Historic Landmark District in the country. Stroll its vibrant Main Street, named a 2024 Great American Main Street Award winner, and you’ll be transported back in time as you explore beautifully restored buildings now home to locally-owned boutiques, cafes, art galleries, and restaurants. The town earned a trifecta of recognition in 2024 as USA TODAY’s Best Small Town in the Midwest (winning in 2025 as well), Indiana Chamber’s Community of the Year, and the highly competitive Main Street America award.

Summer is the perfect season to experience all Madison has to offer, and one of the best ways to explore is aboard the new Madison Trolley Line. This visitor favorite offers a delightful mix of history and convenience, with free downtown loops every Fourth Friday and Summer Sunday through Labor Day, guided tours at 11AM and 1PM on Mondays, Tuesdays, Fridays, and Saturdays, and themed rides like Clifty Days, which pairs scenic routes with hiking adventures at nearby Clifty Falls State Park. The trolley is also available for private rentals and special events, making it easy for groups, families, and couples to explore the town in style while learning its incredible story.

Art lovers will appreciate that Madison is a certified Indiana Cultural District, one of only twelve in the state, known for its vibrant murals, public sculptures, working studios, and frequent exhibitions. The riverfront comes alive with concerts, festivals, and events all summer long, including outdoor movies in Bicentennial Park, the PRIDE Festival, car shows, a weekly farmers market, and more. For those craving adventure on the water, Rockin Thunder River Tours offers a thrilling and scenic way to explore the Ohio River. And don't miss the 75th Annual Madison Regatta, celebrating a long legacy of hydroplane racing with a weekend full of festivities, including a fireworks display and the beloved Main Street parade.

Families and kids at heart can check off summer bucket list musts like a scoop of ice cream from Chillbilly Treats or Scoops, riding bikes along the river, picnicking at John Paul Park, or splashing down the slides at the award-winning Crystal Beach Aquatic Center. Vintage shoppers will love exploring antique shops scattered throughout downtown, and foodies can indulge in everything from classic burgers at Hinkle’s to craft cocktails at upscale restaurants like Red on Main or River Oak Chophouse. Kids and grown-ups alike can enjoy Madison’s newest addition, Vintage Lanes, a family-friendly duckpin bowling alley paired with a stylish, adults-only wine bar, all under one roof. For a laid-back day, grab a cold drink, rent a golf cart from Acree Alley, and take in the town at your own pace. Madison also serves as the perfect launch point for motorcycle and scenic car rides along the REVerie Roads regional trail system, especially the exhilarating Serpent of 62, with 1,000 curves in just 100 miles.

Whether you're dancing to live music by the river, exploring the cliffs of Clifty Falls, or just catching a golden-hour view from the walkable Milton-Madison Bridge, summer here is full of moments that feel both nostalgic and new. Madison’s unique blend of small-town friendliness, cultural depth, and outdoor adventure makes it an ideal destination for weekend getaways, road trips, and everything in between. This season, pack your sense of wonder and come see why so many are falling in love with Madison - Indiana’s best-kept summer secret.

Clifty Falls State Park photo by Bernie Kasper