Lexington, VA: Historic Charm & Valley Views
Saydie out among the rolling hills of the Shenandoah Valley at Great Valley Winery.
From historic college campuses to rolling vineyards, Lexington offers a perfect mix of small-town charm and outdoor adventures.
Historic charm meets puppy-approved comfort at the Abigail Inn in Lexington.
Arrival & Downtown Stroll
We arrived at the Abigail Inn and were immediately greeted with a warm, welcoming atmosphere. The hosts and their three lively kids added to the family-friendly charm, and the pups wasted no time claiming their bed—clearly approving of the cozy space as much as I did.
Archie claiming his new bed while Saydie looks on, hoping to find room to join him.
After a little rest, I took a leisurely walk through Downtown Lexington, one of the most charming and well-preserved small towns in Virginia. Walking the red-brick sidewalks, you can feel how long this town has been welcoming travelers, dating back to its days as a trade stop along the Great Wagon Road.
Exploring the red-brick sidewalks and historic storefronts of Downtown Lexington.
The town’s character is shaped by its two historic campuses: Virginia Military Institute (founded 1839) and Washington & Lee University (founded 1749). Their stone buildings and green lawns add a collegiate warmth to the town .
Historic stone buildings and green lawns at Virginia Military Institute, a cornerstone of Lexington’s character.
I found Seasons, a local favorite coffee shop, where I enjoyed a cranberry spritzer made with fresh cranberry and fresh rosemary syrup, and a delicious artichoke spinach pastry. There was plenty of outdoor seating to enjoy the sun and the downtown atmosphere.
Enjoying a cranberry spritzer and pastry at Seasons Coffee, with outdoor seating.
For dinner, I went to Heliotrope Brewery, a bustling spot that clearly draws students from both VMI and Washington & Lee. The warm aroma of freshly baked pizza filled the air as I settled onto the large outdoor deck with my two pups. The lively energy, friendly crowds, and relaxed vibe made it easy to feel at home. I enjoyed an individual pizza (gluten-free available) and a delicious Caesar salad, a simple and satisfying end to the evening.
Relaxing on the large outdoor deck at Heliotrope Brewery, pizza in hand and pups nearby.
Archie and Saydie on the deck at Heliotrope, watching the lively scene inside.
Breakfast & Morning Coffee
Proof that breakfast doesn’t need to be complicated 🌿 arugula, olive oil, salt, whole-wheat muffin
The next morning at the Abigail Inn, I enjoyed another made-to-order breakfast—an easy, unrushed way to start the day. Before heading out, I stopped by Seasons to grab lunch for later: a roasted vegetable sandwich and creamy pumpkin soup, simple and comforting fuel for a crisp morning on the trail.
Chessie Nature Trail
After breakfast, I headed to the Chessie Nature Trail. It’s a scenic 7-mile path built on an old railroad line that used to belong to the Chesapeake & Ohio Railway (“Chessie”). The trail follows the Maury River and winds past meadows, old bridges, and stone walls. It’s gentle and relaxing—an easy way to enjoy fresh air and stretch my legs.
Scenic riverside views along the Chessie Nature Trail — a gentle 7-mile hike
Roadmap Coffee
Once I finished the hike, I stopped at Roadmap Coffee, a local roaster known for its award-winning beans. I warmed up with a delicious latte while soaking in the cozy café atmosphere.
Vineyard Views
In the afternoon, I drove out to Great Valley Brewery & Winery, tucked into the foothills west of Lexington. After starting with a wine flight inside, I moved outside to Adirondack chairs overlooking the vineyards. With a crisp breeze and long stretches of quiet, it was the kind of afternoon that naturally slows you down.
Saydie and Archie exploring the rolling hills at Great Valley Brewery & Winery.
Lavender Farm & Hike
Next we visited the Lavender Fields at Tantivy Farm. The farm sits on a beautiful hilltop, and I followed a trail through their woods in the back, which led to a small waterfall along a gentle stream. Archie jumped right in for a swim, and Saydie followed! It was a playful, refreshing moment tucked into an otherwise peaceful hike.
Archie and Saydie exploring the lavender farm, taking in all the new sights and smells of the fields, cattle, sheep, and guinea hens
Rockbridge Vineyard
The last stop in the Lexington area was Rockbridge Vineyard, set on what was once a working dairy farm. I enjoyed a flight of local wines with cheese under a canopy as a soft drizzle moved through—calm, cozy, and a perfect, unhurried end to the trip.
What better than local cheese to accompany a flight of local wines outdoors at Rockbridge Vineyard, with rolling vineyard hills as the backdrop?
Charlottesville Stop
On the drive home, I stopped in Charlottesville for lunch at Firefly. The pups enjoyed a special treat from their dog-friendly menu, sharing a small burger, while I enjoyed a delicious meal of my own.
Lexington is one of the Virginia towns we include in Quiet Walks & Slow Travel with Dogs, where nearby stops, walkable streets, and a slower pace shape the experience.
So happy to be home — Archie and Saydie settled into their favorite spots on the couch, ready to sleep!
Some dog-friendly spots we didn’t make it to this time, but would happily return for:
🐾 I loved my time in Lexington and wished we had more time to explore! Here are some dog-friendly spots I’d return to:
Restaurants & Cafes
Glowbowl – Poke bowls with outdoor seating
Brew Ridge Taps – Relaxed taproom with dog-friendly patio
Devils Backbone Outpost Tap Room – Mountain-view outdoor seating
Outdoor & Historic Spots
Boxerwood Nature Center – Trails, gardens, and open fields
Jordans Point Park – Riverfront walking paths and grassy areas
Lee Chapel Grounds – Historic lawn, dogs allowed on leash
Washington & Lee University – Campus grounds, leashed dogs welcome
Virginia Military Institute – Courtyards & pathways
Lodging Options
Fox Hill Bed & Breakfast Suites – Countryside B&B, spacious suites, dogs welcome
Holiday Inn Express Lexington – Central, pet-friendly
Sleep Inn & Suites Virginia Horse Center – Convenient, mid-range, dogs allowed
