The Best Small Towns in Virginia
Throughout 2019, I worked with soo many amazing Small Towns within Virginia and I called it my Small Town Travel Series. Well, I’m finally getting around to compiling a list of each town that I was able to work with! So here is a years worth of travel and what I consider to be “The Best Small Towns in Virginia.”
1. Onancock, VA
Onancock, VA (pronounced O-NAN-cock) is a tiny town located on Virginia’s Eastern Shore. The historic, coastal small-town charm will make you fall in love instantly. As a coastal community, Onancock’s wharf is the happening spot to be in town. With so many unique things to do and see, I was not surprised to hear the huge amount of people who say they come back to this area year after year.
Read more details about this trip here.
My Itinerary:
Day 1:
- Check-in at Spinning Wheel Bed and Breakfast
- Explore downtown Onancock
- Dinner on the Wharf at Mallard’s
Day 2:
- Delicious complimentary breakfast at Spinning Wheel
- Check out Burnham Guides for kayaking and sightseeing tours
- We took part in their Pints and Paddles Tour, which is made up of half of the time kayaking with Burnham Guides and the other half is made up of winery, brewery, and sightseeing visits through The Ugly Oyster Company.
- Relax and Regroup at the B&B – enjoy a glass of wine on the front porch
- Dinner at Blarney Stone Pub
2. Bristol, VA
Olivia and I absolutely fell in love with the charm of downtown Bristol VA. The town is very unique in that the main street yellow lines actually divide the town in half, where one-half of the street is in Virginia and the other half is in Tennessee. Also, Bristol is known as the “Birthplace of Country Music;” and they actually have legal documents to prove it.
Read more details about this trip here.
My Itinerary:
Day 1:
- Check-into The Bristol Hotel
- Explore downtown
- Dinner at Vivian’s Table inside of The Bristol Hotel
- Drinks (and hopefully music) at Lumacs Rooftop Bar (part of the hotel)
Day 2:
- Breakfast and Coffee at Blackbird Bakery
- The Birthplace of Country Music Museum
- Lunch at Taste and a Wine Tasting at Nicewonder Farms and Vineyards (both are located at the same place, inside the gated community of the local country club – and they will be opening an Inn and Spa on site in 2020)
- Explore the area or head on to Abingdon, Va for another day of exploration like I did (more details on this to come soon)
3. Gordonsville, VA
Gordonsville is an adorable small town located just north of Charlottesville, VA. It is another small town that is heavily concentrated with excellent wineries! They also have an adorable downtown with unique shops and pop-ins. Gordonsville is also home to the Fried Chicken Festival, which I attended in May. The town is world-famous for their fried chicken, and it can only be found at this festival held on the 3rd Saturday of May each year. Back in the day, people could get off the train that passes through town just to get a piece of Gordonsville Fried Chicken.
Read more details about this trip here.
My Itinerary
Day 1:
- Lunch at BBQ Exchange
- Well Hung Vineyards
- Explore Downtown
- Check-in at Uphill House B&B
- Tasting at Barboursville Vineyard’s Library 1821
- Dinner at Palladio (located at Barboursville)
Day 2:
- Breakfast at Uphill House B&B
- Get picked up by Central VA Wine Tours at 12 pm at B&B
- Keswick Vineyards
- Reynard Florence Vineyards
- Chestnut Oak Vineyards
- Dinner at Fabio’s Italian Restaurant
4. Lovingston, VA
I was able to spend a weekend in Nelson County VA, which is known for its variety of wineries, breweries, and distilleries! I chose to focus on a specific area within Nelson County – specifically the Lovingston region that surrounds Highway 29. We stayed at the beautiful Orchard House Bed & Breakfast, which was a delightful treat in itself. The owners are so kind, and great at what they do! I was so excited to start this trip (and also a little late) that I got a speeding ticket on the way up, so watch out for that in the area. But here is my itinerary for this weekend wine tasting guide for Lovingston VA.
Read more about this trip here.
My Itinerary:
Day 1:
- Wine Tasting at Delfosse Vineyard & Winery
- Wine Tasting at Brent Manor Vineyards
- Flight of Craft Beer at Wood Ridge Farm Brewery (food truck is available for food/snacks)
- Check-in at Orchard House B&B
- Dinner at Blue Mountain Barrel House & Food Truck
Day 2:
- Breakfast at Orchard House B&B (complimentary for guests)
- Tasting & Tour at Virginia Distillery Company
- Lunch at Lovingston Cafe
- Explore Fortune’s Cove Nature Preserve
- Wine Tasting at Lovingston Winery
- Dinner at Wood-Ridge Brewery & Food Truck
Day 3:
- Breakfast at Orchard House (complimentary for guests)
- Drumheller’s Orchard
- Blue Moon Antique Mall & Bookstore
5. Bedford, VA
Bedford County is located in south-central Virginia, near Smith Mountain Lake. During my time in the area, I was able to stay one night in downtown Bedford and one night at Smith Mountain Lake. This allowed me to see different areas within the region, and they are both worth a visit! Who doesn’t love a town surrounded by a gorgeous body of water??
Read more about this trip here.
My Itinerary:
Day 1:
- Check-in at Longwood Inn in downtown Bedford
- Mountain View Vintage Market (There is a Christmas Market on November 16th)
- Refresh at the Inn
- Dinner at Bedford Social Club
- Beer tasting at Beale’s Beer
Day 2:
- Breakfast at the Inn or stop by Bridge Street Cafe’
- Visit the Bedford Area Welcome Center, get a photo with the LOVE sign, and purchase D-Day Memorial Tickets
- National D-Day Memorial Tour
- Visit the Bedford Boys Tribute Center
- Lunch at Town & Kitchen Provisions
- Explore Downtown
- Leave downtown Bedford and head to Bedford Landings B&B at Smith Mountain Lake
- The owners can give you tons of dining recommendations – I attended an event at Hickory Hill Vineyards. One suggestion is Heath’s Waterfront Grill!
Day 3:
- Breakfast at Bedford Landings
- Sightseeing cruise at VA Dare Marina
- Wine tastings at Hickory Hill Vineyards
- Wine tasting at Ramulose Ridge Vineyards
6. Abingdon, VA
The town of Abingdon has plenty to offer visitors and it has a very walkable downtown area. We stayed at The Martha Washington Inn & Spa, which boasts of historic charm with modern amenities and perks. While staying downtown catch a show at The Barter Theatre (the nation’s longest-running professional theatre) or walk down to Wolf Hills Brewing Company for a delicious taste of locally made beer. But what you definitely don’t want to miss is a short drive to Abingdon Vineyards!
Read more about this trip here.
My Itinerary:
Day 1:
- Check-in at The Martha Washington Inn and Spa
- Head over to Abingdon Vineyards for a Tasting (and maybe a picnic lunch)
- Return to downtown Abingdon and explore
- Dinner at Sister’s American Grill (inside of The Martha Washington)
- See a show at The Barter Theatre or attend a local event such as “Abingdon’s Thursday Jams”
Day 2:
- Free Breakfast for Hotel Guests at Sister’s American Grill
- Get a Spa Treatment or relax by the pool at The Martha Washington
- Lunch at Bone Fire Smokehouse
- Visit Wolf Hills Brewing Company for a taste of local beer
- Explore the Southwest Virginia Cultural Center and Marketplace
7. Madison, VA
The Taste of the Mountains Festival was happening in downtown Madison while I was in town. This was a great local street festival full of crafts, art, music, food, and wine! I highly recommend visiting during this time next year – it’s one of the best street festivals I’ve ever been to. The streets are filled with tents that seem to never end. Everyone was very nice and the weather was great. Madison is full of great restaurants, wineries, and breweries – making it a great weekend getaway!
Read more about this trip here.
My Itinerary
Day 1:
- Check-in at the Ebenezer House Bed and Breakfast
- Day at the Taste of the Mountains Festival
- However, if you decide to visit when there is not a festival in town – explore the downtown area on your own. In addition, here are some wineries that you should visit:
- Lunch at Jenny Lynd’s Pizza (some of the best pizza ever and I am a pizza lover)
- Relax at the B&B
- Dinner at Mad Local
Day 2:
- Homemade breakfast at the Ebenezer House Bed and Breakfast
- Coffee at Cake Krums
- Tasting & Lunch at Early Mountain Vineyards
- Tasting at Blue Quartz Winery
- Drinks (& Music if available) at Bald Top Brewing
- Dinner at Bavarian Chef
8. St. Paul, VA
Wise County VA is located in Southwestern VA (not too far from my previous projects with Bristol, Abingdon, and Marion). Within Wise County are the adorable small towns of Wise, Norton, and St. Paul. I spent the most time in St. Paul, which is where the gorgeous Western Front Hotel is located. With so much to do in one small area, you may never want to leave.
Read more about this trip here.
My Itinerary:
Day 1:
- Check-in at the Western Front Hotel
- Drinks and dinner at Sugar Hill Brewing Company
- Explore downtown St. Paul
- Music at Lays Hardware (20-minute drive from Sugar Hill Brewing)
Day 2:
- Fourth Avenue Baked Goods Café and Bakery
- Tasting and Tour at MountainRose Vineyard
- Lunch at the Corner Diner at the Inn at Wise
- Explore downtown Wise
- Music and Entertainment at the backyard venue at The Western Front Hotel
- Dinner at Milton’s in the Western Front Hotel
Day 3:
- Float the Clinch River (Kayaks or Tubes) with Clinch Life Outfitters
- Day at Leisure/Return Home
9. Marion, VA
Marion, Va is a tiny town located in Smyth County Virginia. However, small towns aren’t what they once were. Marion may be small, but the businesses downtown are thriving. Known as “America’s Coolest Hometown,” this adorable town in Southwestern Virginia is certainly worth a short getaway! So here are the best things to do in Marion, VA.
Read more about this trip here.
My Itinerary:
- Check-in to the General Francis Marion Hotel
- Explore Downtown Marion
- Hesters General Store and Fudgery – incredible homemade fudge
- Just Believe Boutique – great boutique clothing
- Sisters Cafe & Gifts – excellent coffee shop
- Downtown Boutique – great boutique clothing
- & Many More!
- Lunch at Macado’s
- Tasting at Davis Valley Distillery (try the bloody mary… even if you don’t normally like them!!!)
- Explore Hungry Mother State Park (ziplining and beach access available)
- Refresh at Hotel
- Dinner at The Speakeasy (inside of the General Francis Marion Hotel)
- Possibly a show at The Lincoln Theater
Thank you for reading about “The Best Small Towns in Virginia.” I hope you will share this post with your friends & find your next VA Getaway! If you have any questions, please ask! Follow along on Instagram and Facebook for more 2020 adventures.
Until next time,
XO
2 thoughts on “The Best Small Towns in Virginia”