Spend the weekend in the Center of the Universe and discover why Ashland is a small town with a big personality. With a historic train station serviced multiple times a day by Amtrak and conveniently located right off of I-95 and I-295, Ashland is an ideal spot to spend a weekend no matter the time of year.

Begin your weekend with a stop at the Ashland/Hanover Visitor Center, located inside the train station, for help planning your time in town and to pick up information, maps, and local tips. Whether you’re here for a weekend, a week, or more, we hope you enjoy your time with us!


1. Shopping Spree, 2 PM
Stroll and peruse the unique shops in Ashland’s historic downtown for one-of-a-kind finds. For antique and architectural salvage treasures, don’t miss Caravati’s, Thrill of the Hunt, and Hickory Creek Antiques. Have a foodie in your group? Ashland Meat Company stocks locally-made snacks, sauces, and supper fixins’. Along Hanover Avenue, Wagner Jewelers offers custom and antique jewelry and refunkit carries an ever-changing collection of “funky art for your home and person.” Tiny Tim’s Trains & Toys is ideal for kids and kids-at-heart, Center of the Yarniverse for knitters, and Changing Reins for the horse-lovers in your life.

2. Hoppy Hour, 5 PM
Rest those weary shopping shoes at Origin Beer Lab. Sip a microbrew in the beer garden or train and people watch from the front patio. As a favorite locals hang out spot, Origin’s rotating tap list includes seasonal and limited edition brews in a sleek and modern atmosphere.

3. Farm-to-Table, 6 PM
Settle your tab at Origin and head next door to The Caboose Market & Cafe for dinner. Serving seasonally-focused, farm-to-table fare, start your evening with an order of the housemade pimento cheese or smoked salmon dip and round it out with the chef’s nightly special, a grass-fed burger, or farm-fresh salad. Pair your meal with a craft beer or bottle of wine from the restaurant’s thoughtfully curated list.

4. Nighty-Nightcap, 8 PM
Belly up to the bar at The Iron Horse to cap off your evening with a cocktail and live music. The bartenders here have mastered the classics and make an especially mean martini and Old Fashioned. On many weekend evenings, you’ll find local folk, jazz, and acoustic acts perched in the windows-turned-stage of this former department store. In the mood for something with a bit more groove? Huddle Up Sports Bar & Grille is your destination for live music, a lively crowd, and a boppin’ dance floor.


5. Carbs & Caffeine, 9 AM
Wake up and prep for the day with a latte and perfectly toasted everything bagel at The Depot, located right next to Ashland Meat Company. This coffee shop, event space, and art gallery in one boasts a bonafide barista and chill vibes to ease you into your day.

6. History Lessons, 11 AM
Get your bearings and tour the big red Caboose at The Ashland Museum. Learn the history of this railroad town and its origins as a mineral springs resort for city-weary Richmonders in the 1850s and 1860s. Get the full picture with a stop at Hanover County Black Heritage Society, located inside the Henry Clay Inn, which features exhibits centered on the black experience in Ashland and Hanover County. Then set off on foot down South Center Street and the surrounding neighborhood for a walking tour of Ashland’s historic homes.

7. Comfort Cuisine, 12 PM
For lunch, tuck into a warm and made-from-scratch, pot pie from the Ashland Pot Pie Company, located in the back of The Depot. Their perfectly flaky crust and sweet hand pies for dessert are just like mama made, but better. Venture a few minutes just outside of downtown for soul-filling soul food at Around the Table or barbeque and fried green tomatoes at Jake’s Place.

8. Stretch Out, 1:30 PM
Walk off that lunch in one of Ashland’s parks. Stroll Stony Run Trail or the trails around Carter Park. Take the kids to the playground at Pufferbelly Park or fish in the pond at DeJarnette Park. Prefer more idle time in nature? Stop for a while and watch the trains roll by at Railside Park & Trail.

9. Sweet Spot, 2 PM
Ruin your dinner with hand-scooped ice cream or a smoothie at Foodio. Prefer to grab and go? Poke your head into Sugar Fix Bakery for a rotating selection of cookies, brownies, and other sweet treats, or grab a Mexican paleta chocked full of fresh fruit at Los Regios Dulceria y Neveria.

10. Take Flight, 5 PM
Happy hour is made happier at Casa Herradura with their signature margarita flights. Stay for dinner and enjoy freshly made and well-seasoned classic Mexican cuisine in a casual, family-friendly atmosphere. Or stop into Fire & Chicken for an Inca cola, succulent chicken, and other Peruvian specialties.

11. Dose of Drama, 7 PM
Enjoy a movie, live music, or comedy performance at the historic Ashland Theatre. In the mood for a little more drama? Red Vein Escape and Ashland Haunted History Tours will get your adrenaline pumping.


12. Let’s Do Brunch, 11 AM
Finish out your weekend with brunch on the porch of The Henry Clay Inn or the patio of The Iron Horse. Both locations offer trackside dining in classic, relaxed atmospheres, and menus that pay homage to southern classics. Sip the last of that mimosa just as the distant whistle of your train home begins to beckon down the tracks.


The Henry Clay Inn in the heart of downtown Ashland offers comfortable accommodations in a historically-inspired atmosphere. Stately porches and southern charm come together for a memorable stay.

Tru Hotel by Hilton is located conveniently just off of I-95, a few miles outside of downtown Ashland. One of Ashland’s newer hotel properties, modern decor, and familiar Hilton-brand touches make for a comfortable weekend away.