The Wayside Inn in Middletown, VA, has the distinction of being known as the oldest Wayside Inn, Middletown, VAcontinuous Inn in the United States. (There may be some question about that claim.)  When you're there, you can see why. It still has the flair of an early American Inn.  It opened in 1797 for travelers passing through the Shenandoah Valley, and it is open today for modern day travelers.

A number of years ago, I had five office assistants.  During the Christmas holidays, I gave each one a gift of a night at the Inn along with a wonderful dinner there.  They all raved about the accommodations, and they loved the food.  I also love the food at Wayside.  It's always very well prepared, unique in its presentation and delicious to the last bite.

The Inn survived the Civil War as both northern and southern troops dropped in for a respite from the stress of battle.  Stonewall Jackson's valley campaign took place just a Wayside Inn, Middletown, VAfew miles down Valley Pike from where the Inn is located. 

As the Inn entered the age of automobiles, it became known as "America's First Motor Inn."  Valley Pike was transformed from a pot-hole pitted dirt road to an asphalt coated highway, and more and more visitors arrived at the Inn. 

The Inn is furnished with 100s of antiques throughout, and because of that, it maintains its 18th century charm.  The Inn boasts of several dining areas, and it hosts weddings, receptions and local events.  I often took my fitness studio and church staffs to lunch there.  We all loved it so much that it became a regular stop on our calendar. 

If you are passing through the Winchester / Frederick County area, plan to make a stop at the Wayside Inn.  You can feel the history as soon as you walk in the door.  It's a real piece of Americana.

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Mike Cooper, Real Estate Broker, Winchester, VAGive me a call for all your real estate needs, and let's make something amazing happen. 

Mike Cooper @ Cornerstone Business Group, Inc., 888-722-6029

 

Real Estate Sales and Property Management         

 

(Disclaimer:  All grammatical mistakes, punctuation breakdowns and misspellings are purely for your amusement and entertainment.   Feel free to cackle.)                                                                                                

 
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23 Comments on Wayside Inn - America's Oldest Continuous Inn - Middletown, VA

20 Most Recent Comments Displayed Show All

JUN
27
479,096 Points 11 Featured Posts Outside Blog Called Shot Master

I have not heard of this Inn, but liked learning about it.  Thanks for sharing.
6:39pm • #4
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

That's funny, Karen.  Wayside has advertised itself as the oldest since the early 1900s.  I had never heard of the MD version.

It's a great place to stay and eat, Joy.  Drop in sometime.  8-)
7:06pm • #5
477,349 Points 10 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Mike it does look like a great place and cool that you gave each of your office staff an evening there. Have a good one.

Cal
7:15pm • #6
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Thanks, Cal.  It's a lot of fun.  When you're down this way, drop in.  
7:17pm • #7
493,908 Points 75 Featured Posts Outside Blog Called Shot Master

So cool Mike!  I grew up in Clarion, Pa and there was a place also called the Wayside Inn that we visited on occasions just miles from us.  It is one of those fond childhood memories that just sticks with you and the food was spectacular.

This Wayside Inn sounds like a place I'd love to visit.
8:04pm • #8
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Come on up, Jason.  My treat.  
8:11pm • #9
493,908 Points 75 Featured Posts Outside Blog Called Shot Master

Then I'll order expensive ;)
8:38pm • #10
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Everything is expensive there, Jason, but that's alright.  We'll do it anyway.  8=)
8:40pm • #11
164,040 Points 8 Featured Posts Outside Blog Called Shot Master
You have so many more historical points of interest than we on the Left Coast have. It must be very enriching to experience that.
8:57pm • #12
JUN
28
649,820 Points 69 Featured Posts Outside Blog Attended Rain Camp

Hi Mike.  Talk about a story of survival.  Just wonderful.  Thanks.
3:19am • #13
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Oh, it's just a differernt history, Mark.  I was talking to a waitress from CA a while back and I was fasinated at the history she was sharing.  It made me want to take a trip out west.  8-)

How about that, Conrad.  It's still beautiful inside too.  You can feel the history when you walk in the door.
4:07am • #14
648,394 Points 16 Featured Posts Outside Blog Called Shot Master

Good morning Mike. I love historical places and stories. This is really interesting. Thanks for sharing and enjoy your day.
4:31am • #15
670,111 Points 8 Featured Posts Outside Blog Hit Router Called Shot Master

Good morning Mike congratulations on the featured post.  Yep it almost never fails I get up having a cup of joe and someone talks about food.  Well headed to the fridge later
4:32am • #16
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

You too, Sheila.

Enjoy, James.  8-)
5:36am • #17
379,863 Points 84 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Mike - one of the things I love about where I live is all the historical homes and buildings. Thanks for sharing the history of Longfellow's Wayside Inn in Sudbury, MA. I love staying at Inns with so much history and antiques - they are always so charming! I will be sure to stop by if I'm ever in the area! 

10:41am • #18
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

I love those old building too.  They always make feel like I'm a part of history when I'm there.  Thanks for dropping by.  I hope you're having a great day.
10:53am • #19
631,975 Points 3 Featured Posts Outside Blog Attended Rain Camp

Hello Mike,

Wonderful local post on this surviving landmark...the Wayside Inn is a "must see" for anyone touring the area!
4:20pm • #20
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

It really is, Lisa.  Drop in if you're up this way.  8=)
5:31pm • #21
JUN
29
350,354 Points 29 Featured Posts Outside Blog Called Shot Master

Good morning Mike - cool place! I'm tempted to check it out on our next road trip south!
3:43am • #22
554,483 Points 148 Featured Posts Outside Blog Attended Rain Camp Called Shot Master

Come on by, W & J.  We'd be glad to have you.
4:10am • #23

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