Rooftop On Main- Madison, Indiana

07/18/2026

Super excited to start transforming this private rooftop patio into a space our guests will love. Just steps from the bedroom, this will be the perfect spot to enjoy morning coffee, unwind with a glass of wine, or relax after exploring historic Madison. Stay tuned!

07/14/2026

One more reason to visit Madison! ❤️

Madison was just named one of the Top 10 Most Charming Main Streets in the U.S. We’re lucky enough to call it home.

Rooftop on Main is getting close! Keep an eye on our page—our booking calendar will be going live in the next few weeks. We can’t wait to welcome you to historic downtown Madison.

Travel experts share their picks for America’s most beautiful main streets.

07/02/2026

View this afternoon from Rooftop on Main!

Madison Regatta is an important of Madison history. Dating back to the early 1950s, this tradition has brought generations of people to the Ohio River for hydroplane racing, fireworks, music, and memories. From the roar of the boats echoing off the hills to the legacy of Madison’s community-owned Miss Madison, Regatta weekend is one of those traditions that makes our river town so special. Ya gotta Regatta! 🚤🇺🇸

When was your first Regatta?

06/23/2026

Madison has so many great events coming up, and we want to know…

What event are you most looking forward to this year? 🎉

Whether you’re planning a weekend trip, coming in for a festival, visiting family, or just looking for a reason to explore downtown Madison, there’s always something happening here.

Drop your favorite upcoming event in the comments — or tag someone you want to visit Madison with! 👇

We’d love to hear what brings you to town.

06/21/2026

Happy Father’s Day from Rooftop on Main!

We hope all the dads, grandpas, stepdads, and father figures are feeling celebrated today.

We also want to say a big congratulations to Rhonda Arehart Robbins, the winner of our complimentary stay giveaway! Thank you to everyone who liked, shared, commented, messaged, and supported the page. The response has been incredible, and we’re excited to welcome guests soon.

We’re planning more giveaways, specials, and sneak peeks in the near future, so stay tuned.

Congrats again, Rhonda! 🎉

06/20/2026

Thank you to everyone who has shared, liked the page, commented, or sent us a message. The response has been incredible, and we’re so excited to be creating something special here in downtown Madison.

Just to clarify, Rooftop on Main is scheduled to open to guests around the middle of next month. We are still wrapping up construction, and while the upstairs stay is expected to open first, the lower-level restaurant will not be open at that time. We are continuing to collaborate with a local operator to finish that space and will share updates as it comes together.

Here’s a little work-in-progress sneak peek of the bedroom while we finish up the final details. It’s starting to come together, and we can’t wait to share the finished space.

Because of the large number of responses, it will take us a little time to organize all giveaway entries and draw a winner for the complimentary stay. The winner will be announced tomorrow, Sunday, June 21 at 5:00 PM.

If you would like the first chance to book before we officially go live, comment ROOFTOP below or privately message the page.

We can’t wait to host you.

06/09/2026

Who remembers this sign? What was your favorite food there?? 👀

06/05/2026

✨ Madison Date Night Giveaway ✨

We’re giving away the perfect downtown Madison date night at Rooftop on Main!

One lucky winner will receive:

🏡 A free night stay at Rooftop on Main
🍽️ A dinner gift card to enjoy a night out in Madison
🌇 Access to our private rooftop patio for the perfect downtown getaway

To enter:

1️⃣ Like/follow the Rooftop on Main page
2️⃣ Share this post or our page
3️⃣ Comment who you would take with you or tag someone who deserves a relaxing night away

Whether it’s for an anniversary, birthday, date night, or just a much-needed break, this is a great chance to enjoy a special night in downtown Madison.

As renovations are finalized, our hosts will communicate with the winner to schedule a date that works. This free stay is subject to availability and may not be available for festivals, holidays, and select weekends.

Winner will be announced on Father’s Day, June 21st.

Thank you for supporting Rooftop on Main — we can’t wait to welcome you! 🖤

Giveaway is not sponsored, endorsed, or administered by Facebook. Stay date subject to availability. Must be 21+ to book.

06/01/2026

Counters installed ✅ getting close!

05/12/2026

A couple stained glass pieces added recently!