Wayside Inn & Larrick's Tavern

We loved our stay at the Wayside Inn, our dinner at Larrick's Tavern, and drinks/entertainment at speakeasy! The rooms are very historic and be prepared for stairs, but we didn't mind at all. The staff walked us to our room and gave us an overview of the Inn which was great. It truly felt like stepping back into a different age at the Wayside Inn. It's supposedly haunted, and I can see how! The town itself is quaint/quiet but was a great location for us to stay at before heading to Shenandoah National Park.

The only semi-negative was that the walls are very thin, so we could hear every conversation word for word from the room next to us, but overall it was still a 10/10 visit.

We stayed here for its convenience to the historical sites. The INN was very clean establishment. Our room was also immaculate. We enjoyed a tour by Piers of the business. We learned a lot of the history of the hotel and the Middletown area.

Monica has surrounded herself with a very pleasant staff. Anne, Sarah and Mike were outstanding with their bartending and waiting expertise with myself and all the guests. Head Chef Dawn and her staff knocked the food out of the park. The crab cakes were the best I've had in years. Loved it. Monica and the front desk staff were very accommodating. We plan to stay the next visit to northern VA.

Staying in this Inn was like going back in time! Rooms were very clean and furnishings in beautiful condition ( very comfy beds). Staff were very friendly and helpful. If you have any appreciation of early American history, you will love this place. I expected to see Thomas Jefferson walk in.
The restaurant had a limited menu (Tavern fare), but what they had, was delicious!
I felt all prices were very reasonable.

21 years after holding our wedding reception at the Wayside, we returned in Feb 2024 to hold a big birthday brunch. We were pleased in every possible way; from management to staff to setup to food, to facility and to prices charged, we could not have been mote satisfied. I think it very telling that the Wayside has a rating over 8 on a popular travel site while a nearby chain hotel that charges nearly twice as much for a room has a rating of only 4. I will go return to the Wayside for my next special event!

The Middletown Garden Club had their 'after the holidays' dinner last week here. It was great. The food, service and all the workers were just great. When our party was over, all the Gentlemen that were working that night, helped all of us to our cars due to the icy parking lot. So greatly appreciated! Wonderful evening at a great place!

We stayed at the Wayside Inn just before the holidays for a family gathering. It was everything we could have hoped for... great service, delicious food, comfortable rooms, and exciting local history. The restaurant exceeded expectations for both dinner and breakfast (make sure you get dessert. ) The large rooms offered seperate spaces for my my husband and I and are two kids. It's a must stay!

Located in Middletown, VA, the Wayside Inn is the perfect place to stay in the Shenandoah Valley. Its rooms are spotless, the bathrooms modern, the location convenient and quiet, the staff helpful and efficient. Unlike that of the national or regional accommodations, the mission of the Wayside seems to be to give lodgers the very most for their money. During this time of year, the inn's lavish decorations are a bonus. Larrick's Tavern serves delicious food. If it's not open, the Daily Buzz and the Blue Ridge Bakery, both excellent, are only steps away. It's a great place, and I'm already looking forward to staying there again.

The Wayside Inn is absolutely amazing. We booked a week and it was so much fun. They allow you to explore the Inn and the the staff are so helpful and friendly. This place is truly a gem.

Amazing gem, conveniently located close to I-81. The hotel (the oldest continuously operating Inn in the US) is appointed with beautiful antiques and artwork, and each room is individually decorated and complete with comfy beds, soft linens and fluffy towels. Don't miss Larrick's Tavern, which serves up fabulous cocktails and meals (and live music on the weekends!). The staff treats you like family, and makes the experience unforgettable (thank you Monica and Sara!). We will be back!

Absolutely loved this place! If you’re into history and unique places, this inn is for you! So many cool antiques inside too! And if anything is open, they say you’re free to explore. The staff was amazing and made local recommendations. They even told me the history of the place. It’s been around since the 1700s. It’s about $85 per night to stay and the parking is convenient. Super quiet and close to Shenandoah for hiking. There’s a gas station, Dollar General and ice cream place down the street. They offer tea and coffee in the morning and I loved sitting in the rocking chairs on the porch out front.

I did not stay so I can't comment on the rooms. Larrick's Tavern was sooo good! Love the old rooms and even the bar.

We were on a long distance trip and looking for an interesting place to stop at a halfway point. What a charming place with excellent history. We stayed the night, room was clean, beds were comfortable. If you love a hermetically sealed pristine place, this is not for you, but if you like quirky and interesting this place is perfect. There is a great tour included as well. We wished we had time to dine in the 18th century old tiny dining area.

Probably the best spot in Winchester/Middletown area. This rustic tavern and inn is exactly what you are looking for when you want a quiet bed and breakfast. The food is above most of the food I've had in this area and I est out a lot. Please take a moment and support the local community.

We really enjoyed the Wayside Inn. Terri gave us a great tour and was so friendly and welcoming! It was cool to hear about all the history. Our room was really big and furnished in a very nice antique-y way so it felt like staying in history. Great restaurants/coffee within walking distance. We plan to go back soon (and wouldn't have planned to do so if we hadn't liked the inn so much!)

We had our company party here last week and it was beyond expectations! The private room was perfectly sized with a beautiful extra large wood-burning fireplace. The private bar was another selling point. The serving staff was incredible: friendly, professional, wore tuxes! And the food was delicious. We are a wedding industry company so we eat high end catered meals often, yet for many of us what Wayside served was one of the best catered meals we’d had.

The property is beautiful and relaxing. Parking is easy. They even have a rotating art gallery of gorgeous works.

As we left, several people in our party whispered to themselves, “wow, I didn’t realize it was going to be this nice!”

Wonderful historical place to visit. Great food and staff. Thanks for the good info you shared Sara!

This post is for my fellow Harvest Host travelers. Great location, tons of space and a couple of 30amp spots available for a small $. The food is terrific, with interesting cocktails, a good brew selection and relaxing entertainment. If the tomato bisque is available, dont miss it. The place has history from the late 1700's. There is new owner/management who are avidly working to restore the once great reputation the Inn held that was unfortunately tarnished by previous ownership. This was our second stop here in three weeks and while our first visit was great, the improvements in that short time were phenomenal!! I have no doubt the Wayside will be back to landmark status very shortly. Worthy of a stop a support.

What an amazing place with so much history since 1797. Beautifully decorated rooms. Friendly, helpful staff.

Brunch at the Wayside Inn was fantastic. I had the shrimp and grits. It was full of flavor with perfectly seasoned, blackened shrimp, the perfect amount of cheese, and a delicious red pepper flavor. My family had chicken and waffles and loved them. They also had "the norm" with perfectly cooked eggs, sausage, and hash browns. Our waiter was Mike. He attended every need, making sure we were happy and he was so friendly and personable. Top service! The atmosphere is historic, warm, and inviting, with lots of attention to detail. The restrooms were very clean, but since this is a historic building, it is not accessible for wheelchairs. Dining felt very intimate as there are cozy rooms as well as large rooms for parties. The tavern was cool with an old well you could peer down into, but covered with plexiglass for safety. Beautiful grounds. Just a short distance from I-81 Middletown exit, travelers can stop in as they did hundreds of years ago. Excellent food, first class service!