10 Days In Winchester, VA – Here’s What We Got Up To

Shae and I recently spent 10 days in Winchester, VA. We both had to spend quite a bit of that time working, but we did get to go out and explore northern Virginia while there.

With wine tasting, caverns, waterfalls, an apple festival and more, here’s everything that we got up to.

Luray Caverns

We’d visited Luray Caverns back in 2016 and loved it, so wanted to return on the road trip so we could blog about it.

It’s a beautiful and enormous cavern system, so read more about it here and be sure to go if you’re ever in the area.

Address

Luray Caverns, 101 Cave Hill Rd, Luray, VA 22835

Barrel Oak Winery

On our recent post about what to do in Maryland later this year, Gisele commented that she saw we were in Virginia and gave us some recommendations of things to do.

One of her suggestions was Barrel Oak Winery, a pet-friendly winery in Delaplane.

This was a great suggestion. We got chatting to the lady who was doing our wine tasting and she introduced us to a couple of people who are also traveling full-time in their RV (hi Pedro & Tanya!) I sadly had to get back for a video chat that evening as we’d love to have spent even more time chatting to them.

Barrel Oak Winery was awesome though and we’ll definitely return the next time we’re in north Virginia. Shae will also be writing a post about it, so keep an eye out for that.

Address

Barrel Oak Winery, 3623 Grove Ln, Delaplane, VA 20144

Great Falls Park

We’d visited the Luray Caverns a few years ago when my parents came to visit from the UK. During that same visit we took them to Great Falls Park, a National Park just outside of Washington D.C. on the border of Virginia and Maryland.

There are all kinds of trails you can explore in the park which is what we originally intended to do. However, our dog Truffles had hurt herself the week before and her hind leg was still a little tender, so we decided to take it easy and only check out the falls.

Address

Great Falls Park, 9200 Old Dominion Dr, McLean, VA 22102

Shenandoah Valley Apple Harvest Festival

We saw that the Shenandoah Valley Apple Harvest Festival was being held the weekend before we left Winchester, so decided to check it out.

There were various competitions being held over the weekend, including an apple pie taste testing competition and an apple pie eating competition.

There was also an agility course for dogs. Truffles has never been interested whatsoever when we’ve tried getting her to do any kind of obstacles or agility courses, but we used some Greenies (her favorite treat) to tempt her over and through some of the obstacles.

We were about to head back to our hotel, but saw that there was a beer and cider tasting area, so we paid to enter and got to have five tastings. One of them was Pool Boy IPA from RJ Rockers, a great brewery we visited last year in Spartanburg, SC.

The best was yet to come though. We got chatting to a couple of different couples and had a great time getting to know them. Just before we left, one of the couples – hi Paul and Laura! – invited us for dinner at their house. It was incredibly kind of them considering we’d only met an hour earlier, so we said yes and had a wonderful evening with them and their kids. They actually live in West Virginia, so we’re hoping to meet back up with them later this year when we spend a month in WV.

Address

Frederick County Fair, 250 Fairground Rd, Clear Brook, VA 22624

Belle Grove Plantation

One day while I was working, Shae went to explore Belle Grove Plantation in Middletown, Virginia.

Similar to Barrel Oak Winery, Shae will be writing more about her visit to Belle Grove Plantation in the coming days, so keep an eye out for that.

Address

Belle Grove Plantation, 336 Belle Grove Rd, Middletown, VA 22645

Dulles Day Plane Pull

We got really lucky with this one. Shae had heard about the Dulles Day Plane Pull a few years ago and wanted to return in the future. She happened to think of it a couple of days before we arrived in Winchester and it was being held that very weekend.

The Dulles Day Plane Pull is a fundraising event for the Special Olympics of Virginia and involves teams of 25+ pulling an 82 ton plane 12 feet as fast as they can.

In addition to the plane pull, there’s a car show, a truck pull for kids, airplanes you can tour, face painting, other fundraising activities and more. You can read even more about our day at the Dulles Day Plane Pull here.

Address

Dulles International Airport, 1 Saarinen Cir, Dulles, VA 20166

Veramar Vineyard

On our way to Great Falls Park, we stopped by Veramar Vineyard. To save money on our budget and because I was driving, I passed and so only Shae did the tasting.

I therefore can’t attest as to how good the wine was, but Shae seemed to enjoy the ones she tried. The vineyard is also in a beautiful setting in Berryville, Virginia, so it’d be a nice place to stop and have a glass of wine outside while looking at the mountains.

Address

Veramar Vineyard, 905 Quarry Rd, Berryville, VA 22611