To first-time visitors, Ashland appears to be merely a pit stop along I-95 for truckers and weary travelers. But spend a day exploring, and you’ll discover a quaint and delightfully offbeat railroad town.

Railroad Avenue.
Photography by Adam Ewing
Small towns are plentiful in Virginia, and Ashland—located 19 miles north of Richmond—seems to fit the quintessential historic downtown vibe. Towering oak trees, smiling faces; it’s textbook. At first glance.
“I’ve never seen a town with this main street setup. The boulevard, the shops … the railroad going straight through it,” says Maggie Longest, executive director of the Downtown Ashland Association. And yet, in the 7,000-person town of Ashland, it’s commonplace to eat your dinner directly next to the more than 50 rumbling trains that travel down Center Street every day.
Born from the boom of the railroads, Ashland began as a resort town. In the 1840s, a railroad company built a mineral springs resort and racetrack, bringing tourists in from Richmond to visit. Randolph-Macon College, a small private college, moved from Boydton to Ashland in 1868, and the area eventually evolved into a college town. Today, nearby I-95 and Route 1 allow for less than an hour’s drive to bigger cities like Richmond and Fredericksburg, earning Ashland the clever nickname “Center of the Universe.” Longtime residents and newcomers alike are proud of the moniker.
They are also proud of their trains. Every year, the town holds Train Day, when nearly 10,000 people flood the streets in celebration of them. More watch online through the town’s railcams—and thousands tune in regularly from as far away as Australia to watch the trains roll through.
The locomotive enthusiasts make Ashland a bit quirky, but the residents and businesses also give the town an unusual charm. Longest, an Ashland resident herself, understands this all too well. Currently constructing a new town hall, to be completed in 2021, the town opened the architectural drawing to public comment in summer 2018. “People demanded that it have columns to match the train station and a front porch that we could put rocking chairs on. That was a huge deal,” says Longest. “And they got it. It fits the theme of the town: ‘We’re doing it our way.’”

Amtrak train rolling through town.

Wendy Doyle at re•funk•it.

The Ashland Theatre.
At Ashland Coffee & Tea, owner Cate Hawks also walks a fine line between preserving history and trying something new. “We tore down the patio outside to build a new one, and I had people Facebook messaging me the next day, ‘Don’t get rid of the patio!’ I had to tell them to relax and that the patio was coming back soon,” laughs Hawks.
Hawks bought the shop in 2018 and transformed it into a collaborative business space, creating a hub for local women-owned businesses, including Rostov’s Coffee, Carytown Teas, a new yarn store called Center of the Yarniverse, and many others. “The shop is more than just a coffee shop. It’s an iconic anchor in town,” says Hawks. “I want it to be a place where people can come to eat, drink, and be creative.” A perfect breakfast spot for a Saturday morning, try the New York-style bagel sandwich or a cupcake stocked from Pearl’s Bake Shoppe in Richmond. Get there early to beat the crowd of Spandex-clad bicyclists from the Richmond Area Bicycling Association grabbing a quick coffee; Ashland is their most popular weekly ride.
At the nearby gift shop, re•funk•it, customers are greeted outside by repurposed metal garden sculptures, while inside is home to fair-trade jewelry and satchels made from recycled cement bags, all made by artists in Virginia and beyond. Just around the corner on Railroad Ave. is Bell Book & Candle, a charming used book store, and Tiny Tim’s Trains & Toys, a hobby shop filled with model train sets and classic board games, giving visitors glimpses of their childhood.
Next door, The Caboose Market & Café offers both light lunch fare and an impressive selection of local wine and beer. Owner Ian Kirkland launched the shop in 1997 and has grown it to encompass both specialty wines from as far away as Argentina and cheese and wine from local farms and vineyards. Kirkland expanded the back of the shop into a café in 2015, with chef Jeremy Luther serving up favorites like a grown-up grilled cheese made with prosciutto di parma and homemade arugula basil pesto.

Chris Stem at The Ashland Meat Co. at Cross Bros.
Across the tracks sits a town relic that’s been around since 1912. Chris Stem of Harlow Ridge Farm in Hanover and Bruce Johnson of Dragonfly Farms in Louisa purchased the historic Cross Bros. Grocery Store in 2018 with hopes of reviving it. The new Ashland Meat Co. at Cross Bros. has two purposes: half is a trendy event space, while the other half preserves the classic grocery store—including the original aisle signs. “When we thought about a revamp, we kind of wanted to take it back to what it always was: local provisions and locally sourced meats,” says Stem. Known in its prime for its butcher and specialty cut meats, the store now offers grass-fed beef and pasture-raised pork and chicken from Stem and Johnson’s farms and ShireFolk Farm in Palmyra. “Eighty-five percent of our store is local,” says Stem. They even offer their own lines of canned goods and premade meals—the pimento cheese is always a hit.
Ashland has no shortage of historic buildings, and the Iron Horse—housed in an old department store building—is perfect for dinner. Featuring laid-back wood furnishings, a corner bar, and seasonal staple dishes, the fine dining restaurant is a town favorite. It offers modern Southern cuisine, such as shrimp and grits made with Byrd Mill grits or smoked boneless short ribs with whipped potatoes, roasted Brussels sprouts, and a brandy-peppercorn demi-glace. But perhaps the biggest draw of all is the ambiance. “The attraction for a lot of people is this railroad track,” says owner Rusty Stone. “People just love to eat dinner right next to the trains.” Sidewalk café seating fills up quickly; locals enjoy savoring their fried oysters with the breeze of a freight train a couple feet away.
The experience is everything in Ashland, even down to simple things like watching a film. The neon on the marquee of the recently renovated historic Ashland Theatre shines over England Street each night, beckoning people inside. “We like to have it be more than just a movie,” says Jen Chambers, a board member for the Ashland Theatre Foundation. The theater—which operated in pop-up mode from 2014 to 2016 before raising the funds for a full renovation in 2017—shows classic and new movies, live music, and comedy. With a full bar, Art Deco décor, VIP skybox seating, and even themed cocktails for events, the extra details make it worthwhile. On premiere nights, you may even find residents and staff members dressed in costume. “People really get into the spirit of things in Ashland,” says Chambers.
And that’s what makes Ashland so endearing. Between bits of history, unique businesses, local food, and atmosphere, “When you come here, everything is an experience,” says Longest. “You want to come and spend a good couple of hours here and wander around.” Just be sure to plan extra time for train crossings.

The depot clock.

Outside Ashland Coffee & Tea.

Small-scale trains at Tiny Tim’s Trains and Toys.

Cookies at Sugar Fix.
Make It A Weekend
Stay
Henry Clay Inn®
With a history dating back to the 1850s, this Georgian-style inn has 13 guest rooms and a spacious front porch for relaxing. Be sure to try its popular Sunday brunch. HenryClayInn.com
Tinder Guest House
Located above Origin Beer Lab, the Tinder Guest House has three bedrooms, two bathrooms, an eating nook, a gathering room, and a game room. The host provides free homemade breakfast. TinderGuestHouse.com
Do
Ashland Farmers’ Market
The market is open every Saturday from June through October, with special holiday markets in November and December. In the summer, find fresh Hanover tomatoes for sale here. AshlandFarmersMarket.org
Ashland Museum
Step inside an authentic 1926 caboose at this museum. Residents have collected artifacts, collectibles, and mementos to tell the story of the railroad town. Walking tours are available. AshlandMuseum.org
Thrill of the Hunt
Browse refinished modern vintage furniture, home décor, and art at this shop. For savvy DIYers, the shop also specializes in chalk painting and offers workshops to the public. ThrillOfTheHuntVa.com
Eat & Drink
Center of the Universe Brewing Co. & Origin Beer Lab
Never brewing the same beer twice, experimental beers are served in beakers at Origin Beer Lab, Center of the Universe’s sister company and test space. For classics like Pocahoptas, a West Coast style IPA, travel next door to the main brewery. OriginBeerLab.comCOTUBrewing.com
Jake’s Place
A short drive down Thompson Street takes you to this laid-back barbecue joint. The kitchen serves up smoked pork barbecue and delicious baby back ribs—all inside a refurbished 1920s gas station. JakesPlaceAshland.com
Sugar Fix Bakery
You can’t miss this cheery pink bakery on England Street. Since 2015, owner Melinda Foster has crafted detailed cookies equivalent to little works of art. SugarFixBakery.com
This article originally appeared in our February 2020 issue.