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Make the most of your weekend with us in Madison!

Photo Credit: Megan Zink

Explore Madison, Indiana, and experience the wonderful mix of history & preservation, arts & culture, shopping, and dining within its 133-block National Historic Landmark District. Nestled in a picturesque setting along the Ohio River Scenic Byway, the heart of this timeless community is the vibrant Main Street Commercial District where downtown residents work and play. During your weekend visit, discover the charm and the magic that is Madison.


FRIDAY – When the end of your week starts your weekend away.

Entering Madison, take a drive through the Main Street Commercial District to check out the shops & restaurants, then weave through residential neighborhoods of the Landmark District and onto the riverfront to get the full lay of the land. (If you’ve arrived by boat, take a short walk to pick up your rental golf cart and begin exploring!)

Tour one of the impressive National Historic Landmark properties located downtown. Both the Lanier Mansion State Historic Site and the Shrewsbury-Windle House (owned by Historic Madison, Inc.) are beautiful Greek Revival homes facing the river, and both were designed by Francis Costigan, Indiana’s most celebrated pre-Civil War architect and master builder.

Check in to your chosen downtown boutique hotel, guest house, bed & breakfast, or Airbnb and make yourself at home. A delightful evening in the Arts & Cultural District awaits just outside your door.

Dine in at one of several Main Street eateries and enjoy pub fare, upscale dining, café’ or deli soups & sandwiches, and pizza, or head straight to Bicentennial Park for local food trucks and Madison Main Street Program’s Music in the Park. The free, family-friendly event held on select Fridays throughout the summer features local and regional bands rocking downtown at the river. Don’t be shy – join in and dance your heart out!

Keep it going with after-hours libations or live music at small venues within the Commercial District, or wind down at the Fairfield Inn & Suites by Marriott’s patio bar overlooking the Ohio River. This recently rehabilitated 1880s cotton mill is a fantastic example of the adaptive reuse of a historic property.


SATURDAY – All Madison, All Day

Early riser? Head to the riverfront! Chances are good you’ll see a barge loaded with coal plying the river, and you may see one of the American Queen Voyages boats docked and playing her calliope. Go east for a morning run or stroll along the river. Using the new pedestrian lane, cross the Milton-Madison Bridge & back for a great photo opp of the town of Madison. Or go west along the riverfront and pick up Heritage Trail for a more shaded route and walk the steep incline of Indiana’s first railroad, the Madison, Indianapolis & Lafayette.

Prefer to sleep in? Head to Main Street! Start your day at a coffee shop sitting at a sidewalk café table and watching the comings & goings in the business district. Grab a pastry or savor some old-school comfort food biscuits and gravy.

Visit Madison’s beautiful Broadway Fountain, a centerpiece for activities and celebrations, and toss in a coin for luck. Check out local vendors selling producer-only goods around the fountain at Indiana’s oldest Farmers Market. Managed by the Madison Main Street Program, the market operates on Saturdays all year.

Meet a tour guide at the fountain for an architectural walking tour of homes & buildings within nearby residential areas, or enjoy some “retail therapy” at the many locally owned shops and galleries lining the vibrant Commercial District. You’ll find gift and specialty shops ranging from clothing boutiques and art studios to ice cream shops, a handmade chocolate maker, and more!

Stop for a soup & salad lunch, or local Chinese food, or go with a vintage vibe for a hamburger & milkshake at Hinkle’s Sandwich Shop, a hometown tradition serving Main Street since 1933.

Visit and tour America’s only restored 19th-century saddletree factory, Schroeder Saddletree Factory Museum (owned by Historic Madison, Inc.) The tour and exhibits offer a glimpse into the world of the factory worker in Madison’s late 1800s.

Stop by the Main Street Comfort Station where Broomtail Carriage offers horse & carriage rides through the downtown. Learn more about the town’s historic buildings and listen to the driver’s stories of people and events.

Spend a relaxing evening at Thomas Family Winery, a local gathering spot for over 25 years. Enjoy charcuterie, rustic breads, and wine out in the courtyard and live music into the night.


SUNDAY – Ease into another day in the District.

Attend worship service at one of several historic churches within the Landmark District, or enjoy a leisurely morning discovering the Georgetown Neighborhood with a self-guided walking tour. The neighborhood and its collection of buildings are recognized by the National Park Service as a Network to Freedom District for its documented links to the Underground Railroad.

Treat yourself to a one-of-a-kind Sunday brunch at a Main Street restaurant. We’ve got you covered with great options like savory & sweet crepes and pots of tea in an art gallery, bowls & skillets with salsa & over top Bloody Marys in a taproom, or special-of-the-day quiche & muffins in a quaint family restaurant. Count your steps, not your calories!

When the clock strikes Noon, pick up shopping in the Main Street Commercial District and Madison Cultural District where you left off yesterday. There are lots of shops and galleries you won’t want to miss, but don’t forget to look up as you walk along. The colorful streetscape of restored storefronts, blooming planters & baskets, flags & banners, and painted murals tell a story of a town whose business owners, city government, and arts community work in tandem to create Main Street’s charm. Stop at Mulberry Street parking lot and create a memory with a selfie at the Kindness Mural. Featured in the Indiana Arts & Cultural Passport of the state’s 12 Cultural Districts, this community-designed and painted mural is dedicated to showing kindness to one another.

Return to the riverfront for an outdoor sightseeing adventure with Rockin Thunder River Tours. Tours of the Ohio and Kentucky Rivers offer a unique and exhilarating experience for lovers of history, wildlife, and wonderful scenery.

Back on dry land, there’s time for one more stop before you head for home. Visit Sallie’s Small Batch Ice Creams for a sweet conclusion to your landmark getaway. Just like Madison, they offer unique seasonal flavors!

UNTIL WE MEET AGAIN – There’s even more to see and do within Madison’s National Historic Landmark District. Start working on that bucket list for your next visit or come back for one of our special events throughout the year.

We can't wait to see you in downtown Madison!


Written By:

Sally McWilliams

Volunteer | Madison Main Street Program

Author of Sally's View

Posted By:

Austin Sims

Executive Director | Madison Main Street Program

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