Nestled just 20 minutes north of Richmond, Ashland, Virginia, is the kind of place that feels like it was built for cozy weekends. With its walkable downtown, historic railroad tracks running straight through the center of town, and a welcoming community spirit, Ashland offers the perfect blend of nostalgia and modern comfort. At Christmastime, it becomes even more magical!
I had the very good fortune to spend a fun-filled day in June 2026, exploring this charming town of 8,000 kind folks. Come and discover why Ashland is a great destination for the holidays, or really, any time of the year.
A huge thanks to Visit Ashland VA for hosting us and sharing the many things that make your town so unique and memorable!
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Best Getaway Destinations: Ashland
Whether you’re looking for a long weekend getaway or a festive holiday escape, Ashland delivers a “I just stepped into a Hallmark movie” vibe from the moment you arrive.
Because this weekend officially marks Christmas in July, I thought it would be fun to highlight not only the town of Ashland but the special events that make it ideal for a Christmas getaway. Because Ashland is a small town, I recommend booking well in advance to ensure you can visit during one of its most festive seasons!
Why Ashland Makes a Perfect Weekend Escape
Ashland’s appeal lies in its simplicity: friendly faces, locally owned shops, and a main street that encourages wandering. The town’s compact size means you can park once and explore everything on foot.
The two main streets of the downtown area, Railroad Avenue and England Street, are lined with a variety of unique boutiques and cafes. Because trains pass right through the heart of downtown, railroad nostalgia and trainspotting are popular activities.
The Perfect Place to Stay
For a front-row seat to Ashland’s small-town rhythm, look no further than the Henry Clay Inn. Just a mile off the highway, the Henry Clay Inn offers a vastly different experience than the many chain hotels that line I-95.
With a comfortable, cozy vibe, historic charm, and rocking-chair porches, the lodging makes for a relaxed home away from home while remaining just steps from the many sights listed below.
The property has a market on-site that sells beverages and pastries and a restaurant which serves brunch, lunch, and dinner on varying days of the week. While we were there, we had the chance to meet Chef Jeffrey Aquino and sample some of his spectacular sweets.
Chef Aquino came to Ashland following a decade-long stint in New York City, where he worked at a Michelin-rated property, among others. His experience shows. I’m not even a “sweets” girl, but the treats he prepared for us were a delight. The peach upside-down cake was my personal favorite! Fresh, flavorful, with a perfect texture that made me want to savor each bite.
The violet Pavlova with strawberries and vanilla cream and the buttermilk panna cotta with raspberry and lychee were equally decadent. For a beverage, I tried the blueberry “Center of the Universe” spritz while others sampled the strawberry-kiwi margarita.
Even if you opt not to stay at the Henry Clay, I’d make a point of visiting their market or enjoying a meal there. Chef Jeffrey is a critical hire in realizing the proprietors’ dreams of one day turning the Henry Clay into a property worthy of competing with the Inn at Little Washington.
Best Things to Do in Ashland
I recommend starting with a trip to Ashland’s visitor center. It’s located in Ashland’s historic train station and perfectly positioned for wandering the main sights.
The train tracks are a huge draw here! With approximately 50 trains passing each day, the platform near the visitor center is often filled with photographers and train enthusiasts. There’s even a live webcam that people tune into from all around the world!
In different areas around town, you’ll come across these informational signs with QR codes. They’re very informative and provide an interactive way to explore the city.
Across the street from the visitor center, you’ll spy the massive, 3500 pound, bronze Secretariat statue. The great Secretariat was bred by Ashland-native and Randolph-Macon alum Christopher Chenery. Artist Jocelyn Russell created the piece titled “Secretariat Racing Into History”. After a grand tour around the United States, the statue was placed in its permanent home in 2024.
A short walk down England Street, you’ll find the beautifully restored Art Deco Ashland Theatre. Home to both contemporary movies and live stage events, a stop here is not to be missed.
Now backtrack toward Railroad Avenue. Outside the library, you’ll find a granite kugel ball marked as the “Ashland – Center of the Universe”. Former Mayor Dick Gillis coined this tongue-in-cheek phrase to reflect the town’s location along major routes such as I-95 and US 1. The term stuck and is now a huge source of pride for the residents of Ashland!
Across the railroad tracks, one block up on Hanover Street, is the small Ashland Museum and red caboose, where you can learn more about the history of this charming southern town.
Discover the Coolest Shops
I made my way to several great shops while I was in Ashland, and there are quite a few more that I didn’t quite get to. My first destination was Chirp, a delightful little bird shop with a nice assortment of giftable items. I picked up some paintable watercolor notecards for my sister-in-law.
Next up was Center of the Yarniverse, a cute play on the town’s unofficial motto. This store is stocked with every kind of yarn and needlework kit that you could imagine. I found a couple of items that I thought a young neighbor might enjoy and was surprised by a couple of surprises at checkout: a stitch marker charm and a packet of tea!
Caravati’s Architectural Salvage looked awesome but was closed the day that I visited. Tiny Tim’s Trains & Toys looked like a magical destination for kids or hobbyists, while several that I was traveling with stopped at Refunkit and came out with some great finds.
Ashland Good Eats!
Ashland’s dining scene is small but mighty. We enjoyed lunch at Ash & Olive, where we started with the whipped feta appetizer and a bowl of warm olives. Both were excellent, and I would have been content with those, but there was more to come. I opted for the A & O salad while a few in our group got pizza and one tried a panuozzo sandwich. This is a sandwich made with pizza dough, folded in half like a pita. There wasn’t a bad selection in the bunch!
The cocktails and beer/wine selection were also on point. A seasonal blueberry ale was just right for a hot summer day. Beyond the restaurant offerings, Ash & Olive also has artwork from local artists on sale as well as bottles of wine and other shelf-stable edible items.
I was surprised to see such a variety of foods on offer via various other establishments (Thai, Mexican, Peruvian, Southern, Italian) as well as several bakeries and Center of the Universe Brewing. I only wish I had more time to explore a few local standouts including:
- Iron Horse Restaurant. A local favorite offering elevated comfort food and a warm, welcoming atmosphere.
- Taquería Los Altos. Highly praised for tacos and other Mexican favorites.
- Rise & Shine Diner. An iconic Ashland diner famous for its biscuits and friendly service.
- Homemades by Suzanne. Perfect if you love Southern classics and decadent desserts.
Holiday Events
Kelly Franke, Marketing & Events Manager for Ashland, has assured me that for those visiting during the Christmas season, Ashland transforms into a festive wonderland filled with twinkle lights, community cheer, and nostalgic traditions. I spent the day with Kelly and was so impressed with the enthusiasm she has for the place she calls home. The following events are the heart of the town’s holiday magic:
Ashland’s Annual Christmas Parade
A beloved tradition featuring floats, marching bands, local organizations, and plenty of holiday spirit. Families line the streets, kids wave at Santa, and the whole town feels alive with celebration. This year, the event will be held Saturday, December 5, 2026.
Light Up the Tracks
Ashland’s signature holiday event will run this year from November 21, 2026 through January 1, 2027. The buildings along Railroad Avenue glow with over 10,000 coordinated white lights, creating a sparkling, mile-long corridor that feels straight out of a holiday film. Evening strolls here are pure magic.
Other Holiday Activities
The town hosts a small-business holiday stroll where local shops offer seasonal specials, festive décor, and warm hospitality. It’s the perfect time to pick up unique gifts while supporting Ashland’s small‑business community.
Randolph-Macon College offers holiday performances from concerts to theatrical productions. Throughout December, you’ll find pop‑up events, visits with Santa, children’s activities, and community gatherings that make the town feel especially joyful.
But What About the Rest of the Year?
Maybe Ashland just doesn’t fit into your holiday plan. Well, not to worry, there’s plenty to do the rest of the year. The spring months bring Train Day, arguably the next most popular event after Light Up The Tracks. The warmer months also bring Fourth Fridays. Shops open late, farm-to-table fresh fare is available, and there are free live concerts every fourth Friday from March to October.
Amusement park enthusiasts will want to pay a visit to nearby Kings Dominion, and those who enjoy active pursuits will want to check out the paved Fall Line Trail. When complete, the trail will take bikers and hikers all the way from Ashland to Petersburg, Virginia.
Why Ashland, VA?
Ashland, Virginia is the kind of place that reminds you how special small‑town travel can be. It’s warm, welcoming, and filled with simple pleasures made even more magical during the holiday season. Whether you’re sipping cocoa under twinkling lights, browsing festive shops, or enjoying a cozy dinner along the tracks, Ashland offers a weekend escape that feels both nostalgic and refreshing.
What’s your favorite holiday getaway destination? Is there a Hallmark-like town near your home? I love hearing from readers about new destinations to check out!
Hi Betsy. Ashland sounds like the kind of small town that we would enjoy visiting on one of our road trips. We’ve just been talking about where to go next. We’ve been to Richmond, and though there is a lot to do, in the larger cities, we prefer less traffic, like in the smaller towns. I’m also really interested in learning more about the history of our own country. Thank you for sharing, this very inspiring post. ❤️
Hi Christina, Ashland definitely fits the bill! It’s close enough to Richmond that if you wanted to do something there for the day, you easily could, but offers a much cozier, small-town vibe. Seeing the trains come through is really cool and the desserts we tried at the Henry Clay Inn were just insane! Truly top notch. So glad you enjoyed the post. XO, Betsy