On Instagram (follow me @_thepinkchickadee), I have always seen content pertaining to the stunning town of Winchester, Virginia, yet I hadn’t been. HOWEVER, others’ content on Winchester only made my desires to visit this stunning Northern Virginia town grow and grow. Luckily, when my college friend Carlin started graduate school in Winchester, I was given the opportunity to take a day and visit her there! Carlin and I had a GREAT time catching up and enjoying the gorgeous downtown Winchester together on a sunny September Saturday afternoon.
About Winchester: Winchester is a Northern Virginia town in Jefferson County, located not too far from the West Virginia border. It is also in the heart of the Shenandoah Valley and boosts a rich history, specifically focused on the Civil War playing home to Stonewall Jackson’s Headquarters Museum, and lots of nature and charm, too. Winchester has a lot a rich amount of unique culture with a small town charm. With its location in the Shenandoah Valley, mountains are plentiful and so are vineyards and breweries. For my fellow friends living/have lived in the South, it is important to note that Winchester DOES have a Cookout (!!!!).
Getting There: Winchester is located about 90 minutes from Washington, DC and 2 hours from Charlottesville, Virginia. It is easiest to drive to Winchester from its closest airport Dulles International Airport located an hour east or its second closest airport Ronald Reagan National Airport located 90 minutes east. The town is located right off of highway I-81. That all being said, Winchester makes for the PERFECT small town day trip getaway, given its location in the heart of the Shenandoah Valley and proximity to several local vineyards and breweries.
What We Did:
Old Town Winchester – Carlin and I spent most of our time at Old Town Winchester’s open air walking mall, taking in the live music, enjoying the sunshine, and catching up. We started with lunch at Union Jack Pub & Restaurant which was delicious and had a gorgeous bar, before checking out some of the many shops on the same street, including the ultra-adorable Winchester Book Gallery. There was also A TON of super fun live music in downtown Winchester, too, and what I found to be unique is the diverse age range and genders of people playing the music making it so much more charming and wholesome.
Kimberly’s – Just a couple of blocks away from the open air walking mall in Old Town Winchester is the ultra-adorable and VERYYY much a Katie store – LOL! – Kimberly’s. Kimberly’s has two buildings: one which has all-things seasonal, home decor, and Virginia made goods, whether it be plates, magnets, jams, or wine and another with clothing including … Lilly Pulitzer and Barefoot Dreams (!!!). Carlin and I got to meet Kimberly the store owner and buy some Lilly Pulitzer, too. It was just a week after the September 2023 Lilly Pulitzer Sunshine Sale, which Kimberly’s still had TONS of merchandise marked down from. We also got to shop the 2023 Print with Purpose to support Breast Cancer awareness before it hit the Lilly Pulitzer website. Kimberly’s was definitely a favorite of mine, as I LOVED its super fun Fall decorations, merchandise, and *of course* all-things Lilly Pulitzer!
Handley Regional Library – Looking as if it is a European Opera House, the Handley Regional Library also located in Old Town Winchester is a site to be seen. With free access to all visitors, the Handley Regional Library is absolutely STUNNING. It has a uniquely painted dome which guests can climb stairs to to the top of, alongside functioning as a library to those within the Winchester and greater Shenandoah Valley communities. The Handley Regional Library is TRULY a site to see and definitely worth a visit!
Apples – All across town, there are some super fun painted apple structures representing different aspects of Winchester, including its history and charm. Carlin and I LOVED getting to spot *just a few of them* during our time here in Old Town Winchester.
I truly had an amazing time and a blast here in Winchester, Virginia. I am so blessed to have connected with Carlin during my undergraduate years at Meredith College and to have another friend from Meredith up here in the Northern Virginia area. Carlin is truly a blessing! At the same time, I LOVED getting to explore a bit of Winchester with Carlin and learn more about this beautiful little town located in the heart of the Shenandoah Valley. And, I definitely want to come back, too!
XOXO – Katie <3