Southern Belle in Training

Fashion, Travel & Lifestyle Blog || Est. 2012 || Virginia Beach, VA

October 9, 2020

TRAVEL GUIDE: Weekend in Winchester, VA

      Thrilled today to share the perfect Mid-Atlantic fall weekend destination with you: the charming town of Winchester, Virginia. Located right off Interstate 81, just south of the West Virginia state line, Winchester is somewhere I've passed through more times that I can count. But I had never actually stopped and explored until last month! Spoiler alert: Winchester is a darling town and I wish I'd done a rest stop or two here in years passed, or taken the time to do a full weekend here. Luckily- it was better late than never for me to visit!

     Thank you to the Winchester-Frederick County Convention & Visitors Bureau for hosting me for this press trip, and providing complimentary accommodations, excursions and select meals. All opinions in this post are honest and my own. 

Winchester & The Shenandoah Valley:
     The Shenandoah Valley is a 200 mile long region of the western part of Virginia (with a small portion of it extending into West Virginia as well). It's the valley in between the Blue Ridge Mountains to the East, and the Alleghany Mountains to the West. This region of the state is steeped not only in beautiful natural views, but also in Civil War history. The Shenandoah Valley was known as the "breadbasket of the confederacy" during the war, since it is a highly productive agricultural region. There aren't any major cities in the Shenandoah Valley, but there are lots of tiny farming towns, several mid-size to large towns, and a couple small cities (Harrisonburg, which is about the size of Charlottesville where I live, being the largest). Interstate 81 and Route 11 are the primary highways that travel the region north to south. 

     Winchester is located at the northern part of Virginia's Shenandoah Valley, it's exactly two hours from Charlottesville. Its population is just under 30,000, and it's home to a traditional historic downtown area, a small university and many more charming things. My first impression of Winchester was that driving through the downtown reminded me of if Charlottesville and Fredericksburg Virginia had a baby. After visiting for the full weekend, I'd still say that is true and it definitely reminded me of both cities! 

     I was interested in visiting Winchester in 2020 for a few reasons. 1) I'd driven through many times on my way from north to south, but had never taken the time to explore, and 2) small towns and cities in the Mid-Atlantic are my destinations of choice in 2020 during the pandemic! I liked that Winchester had a lot of outdoor and socially distanced activity options that I could share with y'all, as well as a plethora of outdoor dining options in their downtown. My friend Perrin from Charlotte kindly drove up for the weekend to be my plus one and photographer for this trip (she also came with me to explore Norfolk last year). Let's get to the rest of the guide!


     As I mentioned earlier, Winchester is located directly off Interstate 81, a major highway. Not only is I-81 a prominent Virginia route, but it is a prominent north/south route on the East Coast for longer road trips. During my many years of driving with my dad to/from Maine to Charlotte, NC in college, we always preferred I-81 to I-95, since I-95 hits all the major cities and had more traffic. If you're driving north/south, Winchester could be a great spot to spend an overnight to break up your trip!

      Anyways, the most convenient way to get to Winchester I think is definitely to drive! It was exactly two hours from me in Charlottesville, three-ish hours from Richmond and Roanoke, and it is only about an hour-ish from DC (depends exactly what part of the District or NoVa you're coming from, but definitely day trip doable if you're from the DMV area!). If you aren't from Virginia or a nearby state and want to fly here, Washington Dulles International Airport would be the closest at an hour away. 


     Winchester has a wide array of lodging options for a city its size. There are several chain hotels located conveniently right off the interstate, a variety of small bed and breakfasts and inns scattered throughout the nearby countryside (and a few near downtown as well), and then there is a prominent historic hotel right downtown, which is where Perrin and I stayed. 

     The George Washington Hotel is almost 100 years old, built in 1924! While hotel operations did cease for a few decades, it was restored and remodeled in the early 2000s, and reopened as a Wyndham Grand property in 2008. It's the only large hotel in Winchester in walking distance to downtown. Perrin and I really enjoyed our stay here. Not only was the location convenient, but our room was very clean and comfortable! The hotel staff was lovely, and they surprised us in our room with a charcuterie board and water bottles shortly after check-in.

     As far as COVID-19, the hotel is taking all precautions that they can! Everything is being sanitized regularly, you are given a cleaning wipe with your room key at check-in, and there are hand sanitizer dispensers throughout the common areas. The hotel is abiding by Virginia's current mask mandate, requiring staff and guests to wear them in all public spaces in the hotel. Perrin and I did find ourselves taking the stairs to our room over the elevator for most of the weekend out of personal preference- but the elevator is functioning and is an option also!


     I have come to find that Virginia is a state with no shortage of great food, and Winchester definitely lives up to this. Perrin and I enjoyed all of our meals here, and for a small city Winchester definitely has a great variety of everything from casual spots to fine dining. Everywhere that we ate at offered outdoor seating, which we opted for each time for safety during COVID! The three establishments with the N. Loudon Street addresses are all located on the pedestrian mall. 

  • Espresso Bar and Cafe (165 N. Loudoun St. Winchester) If you're looking for a wonderful traditional coffee shop for a quick breakfast, Espresso Bar and Cafe is it! It's located right on on their downtown pedestrian mall. They serve a variety of coffees and teas, and tasty pastries as well! I had a wonderful breakfast tea paired with a cinnamon scone. 
  • Bonnie Blue (334 West Boscawen St. Winchester) Bonnie Blue is a hometown Southern style restaurant with great food and a rustic atmosphere. I actually got to eat here twice! I arrived before Perrin on Friday and met my blogging friend Nicole here for lunch, and then Perrin and I went for breakfast the next day. I had the Pimento Cheeseburger for my lunch meal, and biscuits and gravy for breakfast. Both were wonderful- tasty and filling! 
  • Red Fox Creamery (146 N. Loudon St. Winchester) One thing that has been seriously missing from my life in 2020? Summer visits to local ice cream shops. I've been to the Ben & Jerry's in Charlottesville a few times this year- don't get me wrong, B&J is great at all, but sometimes nothing beats a local spot with homemade ice cream. Red Fox Creamery filled all of my ice cream dreams and more! They had so many fun flavors. I got the chocolate Oreo, which was like 10000% better than a normal vanilla Oreo ice cream.
  • Violino (181 N. Loudon St. Winchester) This was our nicest meal of the weekend! Violino is an authentic Italian restaurant downtown with meals in the $20-30 price point range. Both Perrin and I ordered their house-made gnocchi with different sauces, and we both also enjoyed the chocolate hazelnut torte for dessert. The portions here were so generous that we both had plenty of leftovers to take home, and we enjoyed these as our day two lunch after coming back to the hotel from hiking! Violino has a darling little courtyard area with greenery as their outdoor seating option, which we loved. 

     For a small city, Winchester and its surrounding areas in the Shenandoah Valley have so many fun things to do! I didn't even have time to scratch the surface on half of the local activities just being there for a weekend. I'll list out all the ones I got to do below, and then include extra things in the area that I didn't have time for on this brief trip!

     Shopping downtown: Winchester's pedestrian mall and surrounding streets downtown are filled with unique local shops! I always enjoy seeing when a downtown area still has thriving things like local furntiture, appliance and shoe stores (things that have been taken over by big box stores in a lot of towns)- and Winchester has all of those! Perrin and I really enjoyed and would recommend the boutique Kimberly's. They have a huge array of stationery and fine home items like wedding china, and in a separate building next-door to their home themed location they have lots of women's clothing brands, including Lilly Pulitzer!

     Handley library: One of my favorite things in the world are local libraries- I'm a huge reader and a big fan of supporting everything libraries do in general. Winchester has one of the most architecturally beautiful libraries that I have ever seen- it kind of took my breath away and is worth the visit! Sadly Perrin and I went just a few minutes before it closed for the day so we didn't have too much time to explore, but next time I'm in the area I'd love to spend a couple hours in here and cozy up with a book, and also check out all the floors. 

     Eagle Rock Overlook on the Tuscarora Trail: Our active activity for the weekend was hiking! The Tuscarora Trail is a 250 mile long trail that runs through Virginia and neighboring states- it's kind of like a mini Appalachian trail. Eagle Rock Overlook is located right on the state line of Virginia and West Virginia, about 30-40 minutes from downtown Winchester. It's a 15 minute or so hike from where you park to get to these beautiful views- not a super easy hike but not difficult either. Imagine how beautiful this will be in October with foliage!
     One note about this hike: it is very much off the beaten path. My phone maps app actually got us lost for a good hour or so on some private dirt roads, which was a little sketchy. We finally made our way to the right dirt road and found the trailhead, but just beware this can be a bit hard to find. But I think the hike was worth it!

     Belle Grove Plantation museum: We did a tour of Belle Grove Plantation in the nearby town of Middletown as an afternoon activity. This was a working plantation in the 1700s and 1800s, and there was a Civil War Battle fought directly in front of the house! Sadly this is a plantation that did utilize enslaved labor, but I thought the Belle Grove staff did a great job of highlight the sad realities of that, without glamorizing slavery in any way if that makes sense. If you're a Civil War history buff, this should be a must-visit. 

    Valerie Hill Vineyard: You know I love my Virginia wine! Although I go to Charlottesville wineries frequently, I also love visiting ones in other parts of the state when I travel. There are a variety of breweries and wineries in the general Winchester area. Perrin and I decided to check out Valerie Hill, in the nearby town of Stephens City. This was a small but elegant winery with a wide array of reds, whites and blends. I appreciated the fact they had ample outdoor seating and space for social distancing! There was also some live music happening on the Saturday afternoon that we were there. 

     Family Drive-in Movie theatre: If there was a list of 2020 comebacks, I think drive-in movie theaters would take the number one spot. What a year for this type of theatre! The Family Drive-In in Stephens City is huge, there are two giant screens that show different movies at the same time. There was a concert happening on one screen the night we were there, so we saw Tenet on the other screen, one of the few newly released movies of 2020. The movie itself wasn't my cup of tea (it was a very odd film! Haha), but I loved the drive-in experience! Sitting under the stars and enjoying movie popcorn for the first time since last winter... magical! It made me sad that this was the first and probably only time I'd go to a drive-in until next spring.

     (Seasonal fall activity) Sunflower field at Homestead Farm at Fruit Hill Orchard: This one is a fall-only activity, although I do think their farm store would be fun to see year round. All of the sunflowers were in bloom at the Homestead Farm at Fruit Hill Orchard while I was there! I could've stayed in them for hours and hours enjoying the beauty. 

     Museum of the Shenandoah Valley: One of the most unexpected things that I enjoyed during my visit to Winchester was the incredible Museum of the Shenandoah Valley. I could've spent a full morning and evening here and probably still had time to explore! The Museum is comprised of the main indoor building, and the most beautiful gardens and outdoor space that surround it. 
     There is currently an exhibit called Big Bugs by artist David Rogers on display in the gardens. Want to know something crazy? David Rogers is one of my dad's childhood best friends! I've known him my whole life, and with my family I've seen the Big Bugs exhibit at other gardens and museums over the years (last in 2016 with my dad in Florida!). I had no idea the exhibit was in Winchester currently so this was a delightful surprise to enjoy, and my dad got a huge kick out of it when I texted him. The gardens here are beautiful and maintained so well.
     The indoor part of the museum is amazing as well! I wish I hadn't been so pressed for time to get back to Charlottesville because I could've spent a lot longer in the exhibits. The Shenandoah Valley is such a unique part of the state, and I love that this museum deep dives into the history and culture of this part of the state. 

     Learn about hometown star Patsy Cline and visit her grave: I saved the most meaningful to me personally for last! I am a big fan of Patsy Cline and have been since I was growing up. Some of my most fond childhood memories are listening to a cassette of her greatest hits in my mom's old station wagon! I loved getting to visit the Patsy Cline museum in Nashville last year. Patsy is originally from Winchester- that's actually where she made her musical debut on local radio before moving to Nashville! She grew up in poverty and has an amazing story. 
     Her childhood home is now a museum, but sadly it has been closed for most of this year due to COVID. I would love to go back to Winchester to see this once it re-opens! There are two things you can do currently though to honor Patsy. One is to check out the small exhibit about her at the Winchester Visitors' Center- I really enjoyed seeing it and learned some new things. You can also visit Patsy's gravesite. It isn't very flashy and blends in with the rest of the cemetery, which I feel like made it all the more meaningful to see. 

     Other things to do in Winchester: 
  • Visit more wineries and breweries 
  • Go horeseback riding
  • Enjoy a nightcap at the jazz bar at the George Washington Hotel (we hoped to do this but were too tired the first evening!) 
  • Enjoy apple picking or a pumpkin patch
  • Take a guided walking tour of downtown
  • Visit the Shenandoah Valley Civil War Museum and more battlefields 
  • And MORE!

     Thank you again to Winchester Tourism for hosting me for this fun weekend press trip. I hope you enjoyed learning more about this historical and friendly spot in the Shenandoah Valley. I felt very safe to visit here during COVID and appreciated the plethora of outdoor activity options and the safety measures being taken by local businesses!

     God Bless,

     xoxo Annaliese 


1 comment

  1. This is so helpful! Winchester looks like a fun spot to visit. I didn't know Patsy Cline was from there.


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