Who doesn’t love a good story? Sometimes, you visit a place and just know that each street is steeped in culture or significance. Ashland happens to be one of those places. Trains and trails, historic buildings, and notable districts — Ashland has quite the story to tell.

Ashland Theatre

Any town full of tales tends to feature a grand marquee, and Ashland doesn’t disappoint. The Ashland Theatre, once considered an endangered historic site in Virginia, was restored to its original glory in 2018. This space has all of its original 1940s charm but with modern conveniences such as state-of-the-art technology, luxurious seating, and concessions that feature food and alcohol. Catch a concert, classic movie, or first-run blockbuster in this intimate, historic landmark.

Ashland Visitor Center and Train Station

Ashland is a train lover’s dream. Many traveling families break up a long drive by taking the kids to the downtown Visitor Center and Train Station, which celebrates its 100th Anniversary in 2023! It’s a perfect exit for a welcome break. There, visitors can view passing Amtrak trains, explore a working train station, and learn more about why the town is known as the “Center of the Universe.” Discover their maps, historical markers, and train memorabilia on display while taking in the scenery.

Berkleytown Historic District

Ashland, like many places across the country, once adhered to racist and unequal laws. During Jim Crow, Black residents of Ashland were barred from living in homes within city limits. Rather than adhering to these policies, the Black community built homes right outside of Ashland so that they could continue to work their jobs. This neighborhood became known as Berkleytown, a hub for education, shopping, and business. Today, Berkleytown is a nationally recognized historic district that continues to be tight-knit and full of community pride.

South Center Street

If architecture from another era piques your interest, Ashland’s South Center Street has ornate and interesting homes that speak to the history of the town. These houses feature unmatched artisanship and distinctive details unique to each individual home. Victorian, Queen Anne, and Greek revival style homes just scratch the surface of the differing styles, all of which add to the beauty of the neighborhood.

Randolph-Macon College

One of the most beautiful campuses in the country calls Ashland home, and its history couldn’t be more notable. Randolph-Macon College is the oldest continuously running college in the United States. Though originally located elsewhere, Randolph-Macon moved to Ashland to flee the destruction caused by the Civil War. The stunning 150-acre campus is fascinating to explore by bike or on foot where the splendor of its picturesque setting can be fully enjoyed up close.

The Henry Clay Inn

If you’re looking for a place to stay that also has a rich tradition and compelling backstory, visit the Henry Clay Inn. Originally known as the Ashland Hotel, the first iteration was built in 1858 as a weekend country getaway before being destroyed by fire in 1905. A second hotel, named after famous presidential candidate Henry Clay, opened the following year. It was a huge success, hosting college student dances and balls or serving as inexpensive housing for newlyweds before tragically burning down in the 1940s. The present version was erected in 1992 as an exact replica of its predecessors and houses thirteen guestrooms, a parlor, and a banquet room serving brunch, lunch, and dinner on the weekends.

Ashland Museum

Born out of the town’s 150th anniversary celebration, what started as a gathering and display of historical information related to Ashland’s history became a concerted effort by a small group of locals known as “The Ashland Museum Project” to move forward with plans to create a museum.  The group has continued to grow and now houses numerous spaces such as the Red Caboose, which is now open to visitors, as well as 105 Hanover Avenue, a space to present exhibits and history. As a nonprofit with broad community support, the Ashland Museum continues to grow in a manner benefiting the storied traditions of the town.

The Hanover County Black Heritage Society

With a focus on education and preservation, the Hanover County Black Heritage Society works steadfastly to uncover local black history, protect time-sensitive relics, and inform the public of the rich traditions and backstories of the Black community in Hanover County. They publish numerous monographs on African-American history and families in the area, in addition to creating a traveling exhibit, placing historical markers, and working on numerous other projects of importance in and around Ashland.

Historic Downtown

The beauty of historic downtown is that so many original buildings or antique spaces have been preserved or repurposed into bustling and successful restaurants today. Trackside Kitchen and Wine, a recently updated modern wine bar and restaurant, was once a segregated movie theatre for Ashland’s African-American community. Iron Horse Restaurant, a modern Southern food concept with steaks and seafood, used to house D.B. Cox Department Store. The funky and inventive brewery, Origin Beer Lab, had a first life as Hughes Drugstore, while Ashland Meat Company provides the best locally sourced meats and provisions while embracing the history of 100-year-old Cross Bros Grocery. Each of these storied locations offers delicious food sure to enhance your overall experience in Ashland.

Trolley Line Trail

A trolley between Richmond and Ashland used to bring visitors, students, and businesspeople between the two locales before it ceased operations in 1938. Now, nearly 80 years later, the historic Trolley Line Trail is being repurposed as an off-road path between these areas once more. The big difference is that the new trail, made up of a boardwalk and asphalt path, will host cyclists and pedestrians as part of the larger Fall Line Trail, which when complete will span 43 miles from Ashland to Petersburg.

See Ashland’s History Today

Whether it’s historic landmarks, revitalized walks and trails, or modern updates on significant properties, Ashland has a history that needs to be experienced. Visit here today and start planning your journey into Ashland’s past.