Wayside Inn

I enjoyed the historic hotel. My room was comfortable. I highly recommend staying when the tavern is open. I did not. The hotel was locked when I arrived. I called a number on a sign at the door and was given a code to get into the hotel. There were no employees on site until the next morning.

Great, Friendly, Knowledgeable, Willing to please, everything you want in hotel staff. The staff may be limited but at no time was there a need that wasn't met. The front desk clerk, Kat, was always smiling and full in information. Peirce provided a tour and history of not only the hotel/Inn/Tavern but also local history as well. The bar staff jumped in and helped the wait staff when our very large group (from Vermont to Florida to Illinois) all decided to have dinner in the restaurant at the same time. I absolutely would stay here again and recommend this to others.

We went in for dinner, were greeted by a server who was brand new and, after an hour and ten minutes still did not have what we ordered . All we got were apologies. No free drinks or chips or bread or anything thing was offered except excuses and “just 10 minutes more” assurances that never delivered. We got up and left and would never go back. FYI, the drinks are way overpriced.

The Location is very convenient to the I-81. The parking was Big Rig friendly. The community is Historic, quiet and safe. We are at the Tavern and as our meal was being prepared, we got a private tour of this Historic landmark. Beautiful period furniture and decor. The meal at the tavern was excellent. Our server was attentive and friendly. I had the best French Dip meal ever with home made chips and a frosty beer. My wife ate a delicious Crab cake sandwich and enjoyed her freshest and flavorful meal. Come visit and enjoy a meal in this Historic Inn. You won’t be disappointed. Cheers DJT

Take a pass - My wife and I came in about 9:00 on a not busy Friday evening. We waited by the door unnoticed. A waitress walked right by us, again without acknowledging our presence; I stopped her a few feet after she passed us and asked her about seating; wherever you want was her reply as she kept on her way. We found a table (easy the place was nearly empty) and saw that there was live music, but at 9:00 the band was packing up. The same waitress came back a few minutes later and told us that the kitchen is open, but the bar is closed, so if we wanted a cocktail we would need to go downstairs to the "speak easy". I asked if we could get served food downstairs and the short reply came as "no". We just left and went to a different restaurant. I was happy to spend my dollars in a different location that cares about their customers experience.

Having gotten married in Winchester, VA 25 years ago, we decided to revisit the area to celebrate our anniversary. But we wanted something other than a chain hotel for this special occasion. We were intrigued with the idea of an historical inn, so we booked our stay at The Wayside Inn. Upon arrival, we were greeted by Monica and noticed the Christmas decorations throughout the common areas. Piers also popped in to be sure we were being attended to. Monica gave us a quick tour of the first floor, then took us to our room on the second floor. It's interesting imagining all the people, famous and regular folks, who have stayed at the Inn throughout its history. Descending the staircase from our second floor room, I told my husband, "This is like being on a Hallmark Christmas movie set!" That was fun thinking about! We ate several meals in Larrick's Tavern, and enjoyed each experience. We enjoyed chatting with Ricardo, who served us most of the time. We definitely plan to return and enjoy the area and hospitality at The Wayside Inn & Larrick's Tavern!!

Several friends and I booked the Wayside Inn to be close to a nearby trout fishing stream, but we were delighted by its welcoming staff and fascinating historic hotel structure. Our bed was most comfortable, the inn spotless and the entire town of Middletown walkable and friendly. We look forward to returning to the Wayside Inn!

This is a very beautiful quaint inn. The room was clean and comfortable. We stayed in #3. The staff was friendly and the check in/out is simple. We had everything we needed. Dinner at the adjoining tavern was delicious, as well.

From the moment we walked into the front patio, we felt welcomed by this beautiful inn (the oldest continuously operated in the US). Rocking chairs and umbrella tables invite you to sit and take in the relaxing atmosphere. We were greeted by Terry and Monica who told us a little of the history and showed us the coffee station, which is always open and stocked with snacks. We stayed in the former Inn Keeper’s room, which is absolutely gorgeous, with a 4 poster bed and beautiful antiques throughout the 3 rooms. The biggest hi-light was Larrick’s tavern, located onsite. From unbelievably delicious meals (prime rib & short ribs for dinner, and perfectly prepared eggs Benedict for breakfast), to live music and hand crafted cocktails, the Tavern provides a unique experience that is hard to top. Sarah expertly makes each guest feel as if they are the only one and elevates the dining experience. I can’t recommend the Wayside Inn enough! We will be back!