Pets, Places, & Things, Road Trip

An Afternoon in Old Town Winchester

By Bob Tagert

Another month and another Road Trip to explore what lies beyond Old Town Alexandria. Since I arrived in Old Town some 45 years ago there have been many changes, but none like what we have seen in the past two years. In that short time the closing of the 100 block of King Street occurred and the beginnings of a pedestrian mall, so to speak, was created. This was not a sudden epiphany, but had been studied for years. The cause and effect of the pandemic hurried things along.

Although the end effect of the street closure and additional outdoor space for businesses is yet to be determined, we decided to take a road trip to Winchester, Virginia and visit their Walking Mall. It shows that Winchester encountered some of the same issues that Alexandria faces now in the beginning.

In the early 1970’s Loudoun Street was the heart of Winchester’s shopping district. A few of the downtown businessmen came up with the idea of converting the street into a two block pedestrian walkway. An advisory board was created to oversee the special district. In 1974, the Loudoun Street Walking Mall was born.



Like Old Town Alexandria, poor downtown drainage resulted in frequent occurrences of high water along the newly created pedestrian mall. The mall remained in a state of flux until 2013 when the city replaced the downtown’s underground water system, which at the time was the third oldest in the United States.

Today, the Loudoun Street Mall features cultural events, concerts, outdoor screenings of classic movies, lamp posts with banners displaying works by local artists, holiday celebrations and much more. There is a Civil War Museum and many historical locations throughout the Mall as well in the blocks surrounding it.

We went to visit the Mall during the week as we understood that it is pretty crowded on weekends. The first thing I noticed was the four Autopark’s around the Mall which provided abundant parking at a very low cost – $1 per hour. Bonus!

As I eased my truck into my parking place we enjoyed the two minute stroll to the Mall itself. Since it was lunch time we looked for Mexican (Lani’s favorite) and landed at El Centro Mexican Restaurant and found a table on their patio. Our waitress, Susan, was prompt to the table and soon we were enjoying the sunshine as well has our margaritas. The food was excellent! There are places offering every kind of cuisine lining the both sides of the Mall. Lots of outdoor dining space for sure.

After lunch we took a short walk to soak up the atmosphere of the Mall. Although it is only two blocks long – they are really long blocks compared to those here in Alexandria. The footing is all brick and you encounter a drain every so often which has solved their high water problem. Toward one end of the Mall is a Splash Pad, a respite from the heat on hot summer days. It was up and running but the weather was a bit cooler than it had been so there weren’t any kids or overheated adults taking advantage of it while we were there.

One of the fine stores we visited was Mountain Trails Quality Outdoor Outfitters. This place is great with just about everything you need for that outdoor adventure. From where you sleep, food you make and the utensils necessary, to the clothes you need as well as the necessary climbing gear. Owner Garry Green and his puppy Bennie gave us a tour of the store as he told us about his vision for this store and the sister store in Front Royal and another on the horizon. Watch for a full blown Business Profile on Garry soon.

It was now time for a libation and what better place to unwind with a cocktail than in a bank, and we found two right across from each other. The first we enjoyed was Union Jack in the old Union Bank. This place is beautifully remodeled and very comfortable. From here we headed across the street to another building that said BANK on the front that has a newly opened bar and restaurant, Willie Sutton’s Saloon. Upon walking in the open door, we were told to check back after 3 pm. More on this later.

By this time our former layout and design guru, Lauren, texted that she was at her new place of employment, Dividing Creek Brew Pub. She is now in a management position with all of the creative design duties involved in opening a new venue on her plate as well. Dividing Creek is located on the Mall and is serving the brews that they are conjuring up on site. They were still in the process of getting the final touches pulled together when we were there. Neither of us are craft beer drinkers but the two that Lauren pulled for us were both amazingly good. Please check them out on your visit.

We made it back to Willie Sutton’s to see what all of the hype was about. It appears that Willie Sutton was a famous bank robber in the early 1900’s and the proprietors here have taken that theme to heart. The interior is very nicely appointed and they are in the process of incorporating the vault into the décor. This is a beautifully laid out bar with many fine choices. I was lucky enough to find a five year-old Plantation Rum. I liked this place.

One block from the Loudoun Street Mall is the historic George Washington Hotel. The hotel opened in 1924 to great applause but over time the business began to dry up and it closed in 1978. The building underwent a $30 million renovation and reopened with 90 guest rooms in 2008. It is now operating under the Wyndham Luxury Hotel umbrella. We have stayed at the George Washington and it is very nice indeed.

Today the Mall boasts over 35 restaurants in the downtown area as well as 75 stores and salons. Like Alexandria, the Loudoun Mall also has its own Farmers Market. Our time was limited since we had to make this an afternoon trip instead of an overnight stay, but the next time we are taking time to explore the highlights the town of Winchester has to offer and maybe even check out the market.

The Loudoun Street Walking Mall in Winchester is a great day trip destination and has enough to occupy you if you choose to spend the night. In addition to the Mall there are a number of historical buildings, museums (Patsy Cline’s house is a museum here) and sights in the immediate area that we will save for another Road Trip column.

Reaching Winchester is a nice drive once you clear all of the traffic lights on Route 50 in Chantilly. The drive is about 80 miles so it falls under the heading of “reasonable” with today’s gas prices. One drawback is always the construction Route 66 and it wasn’t bad the day we went. We arrived in about an hour and a half!

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