The Historic Wayside Inn 1797

10/11/2026

10/10/2026

Something is getting a fresh look at the Wayside Inn! 🖤

We’re excited to start making some thoughtful improvements around the property while keeping all the historic charm that makes the Wayside so special. We have lots to look forward to, and this is just the beginning!

Want to see the updates for yourself? Join us for our Ribbon Cutting on Thursday, October 15th at 4:30 PM as we celebrate four ribbon cuttings that day: Billy Sous, Clem's Kitchen, Middletown Mercantile, and the Wayside Inn!

We’d love to celebrate with you!

10/01/2026

A little extra fall charm has made its way to the front of the Wayside Inn, all thanks to our friends at Beatty Farms LLC. 🧡

We are so grateful to the Beatty family for generously donating these beautiful pumpkins, not only to the Wayside Inn, but throughout Middletown to help make Main Street feel a little more festive for the season.

Beatty Farms is one of those special local families that truly cares about their community, and we feel very lucky to have them right here in Middletown.

Be sure to give their page a follow, check out the events they have coming up, and stop by the farm for your pumpkins, fall decor, and Halloween decorating needs this season.

Thank you, Beatty Farms, for helping make our little town feel even more special this fall. 🍂

09/23/2026

A familiar view, decades apart. This photo of the Wayside Inn from the 1940s gives us a glimpse of what the Inn looked like all those years ago, compared to the view we see today.

The wayside has stood here for centuries, welcoming generation after generation through its doors. It’s pretty special to look back at moments like this and see one small piece of its long history.

🎞️ Historic photo featured in More Images of the Past: A Photographic Review of Wi******er and Frederick County, Virginia.

09/11/2026

We have a little Wayside mystery we’re hoping someone can help us solve!

If you’ve been coming to the Wayside Inn for years, you may recognize this mug. You might even have one tucked away at home!

These mugs date back to the time when Leo Bernstein owned the Wayside Inn, and each one has the same number stamped on the bottom. We believe the number may have had a special meaning to Leo, but we haven’t been able to figure out exactly what it was.

So we’re turning to those who remember the Wayside from years past. Does anyone know the story behind the number?

If you know anything about these mugs, or have one of your own, we’d love to hear from you!

09/03/2026

A new chapter at the Wayside Inn. 🤍

For more than two centuries, the Wayside Inn has stood at the heart of Middletown, welcoming generations through its doors and holding countless stories within its walls. Today, we’re very excited to share the beginning of its next chapter.

After spending the past year bringing new life, incredible food, and a true sense of community to Clem's Kitchen, Bill and Amanda Whitson have officially taken over management of the entire Wayside Inn operation.

For Bill and Amanda, this is about much more than managing this historic property. It’s about caring for a place that means something to the community they love.

Amanda’s roots here run especially deep. She grew up in this area as Amanda Clem, the name that later inspired Clem’s Kitchen. Years ago, she also had the opportunity to work under longtime Wayside Inn owner Leo Bernstein, who took her under his wing and taught her so much about events, business, hospitality, and bringing people together. That experience left a lasting impression, making it especially meaningful for Amanda to now help lead the place where she learned so much.

If you’ve met Bill and Amanda, you know the heart they bring to everything they do. They believe in teamwork, community, and creating places where people genuinely want to gather.

And that’s exactly what they hope to bring to the Wayside Inn.

The goal is to honor everything that makes this historic place so special while giving it its heartbeat back. Clem’s Kitchen will continue serving the food and hospitality you’ve come to know and love, while the entire team looks ahead to more events, celebrations, music, gatherings, and reasons to fill these old walls with people again.

We hope you’ll join us in congratulating Bill and Amanda Whitson on this exciting new chapter.

And if you’d like to celebrate with us, join us tomorrow night, September 4th from 6:00 to 8:30pm for Boots & Biscuits - with food, drinks, line dancing, and local vendors throughout the Wayside Inn. It’s just a little glimpse of what’s to come, and one of the many gatherings we plan to have here.

The Wayside Inn has a lot of history behind it. We can’t wait to show you what’s ahead.