How to bike and wine taste as a family in Middleburg, VA

A few years ago (pre-baby) we discovered an area in Virginia where the wineries were close enough together that we could easily bike from winery to winery. One winery even said there was a “bike and wine taste tour”.  We have been trying to find this area since we moved back and low and behold, this weekend we did!

Wine tasting - Adventure Family in Motion
Wine tasting – Adventure Family in Motion

It was about 50 degrees outside so we loaded the bikes in the UAV and  headed northwest to an area near Middleburg, VA. The hour and a half drive took us on the backroads passing an awesome craft brew shop called Crafted.  It shares a parking lot with the only diesel gas station in a 15 mile stretch so we were in luck by finding both of them. Crafted wasn’t open yet so we made a point to stop on our way home.

Crafted
Crafted — Haymarket, VA

Just outside Middleburg lies the very small town of Aldie, VA.  The Aldie Mill Historic District had a nice quaint feel. Although, if you blinked you would totally miss the town.  While driving along, we noticed the all to familiar smell of  a smoker, bellowing out  the smell of the BBQ Master’s latest offerings at the Aldie Country Store.  Varun Parti is definitely a BBQ Master! We feasted on two massive plates of BBQ smoked ribs and 2 pints of mash potatoes and macaroni and cheese.  With an amazing lunch in our bellies we were sure to get a long ride in.

BBQ Master
BBQ Master
BBQ Master
BBQ Master
BBQ Master
BBQ Master
HUGS - BBQ Master
HUGS – BBQ Master
BBQ Master
BBQ Master
BBQ Master
BBQ Master

We first stopped at Chrysalis Vineyards which sits 1.5 miles off hwy 50 on a rutted single lane dirt road. We pulled into a picturesque setting with a pond, rolling hills and plenty of seating. There is a nice place for families to corral the kids while the parents can sip on a  glass of wine, play bean bag toss or have a picnic.

Chrysalis Wineyard
Chrysalis Vineyard
Chrysalis Wineyard
Chrysalis Vineyards

From Chrysalis Vineyards we drove a few miles down 50 to Greenhill Winery & Vineyard (although you could bike this portion, the road is a little rough at times).  Sitting directly off hwy 50 on a 1/4 mile long driveway, The Greenhill Winery and Vineyard was where we decided to start our cycling trip. While Donald unloaded the bikes I got us a nice glass of Syrah for sampling and pre-ride motivation.

Adventure Family In Motion
Adventure Family In Motion

This winery loop is a relatively easy 7 mile bike loop, with the primary difficulty being not tasting to many glasses of wine to continue on with the adventure.  You can start this loop by heading out of Greenhill Winery and turning left on US 50 for approximately 1/2 mile until you come to your first dirt road on the left named Parsons Road.  Parsons Road is a quiet dirt road with limited to no traffic, perfect for a mountain bike, hybrid or cyclocross bike.

Greenhilll
Greenhilll Winery

At the “T”in the road turn right on Halfway Road and start up a gradual hill. Before you know it, you will be at Boxwood Estate Winery and it is time to taste some more wine. Boxwood has a very modern layout with a wine cave, a picnic area and a circular tasting room.  Skylights and white paint fill the rooms with immense lighting and the wine cave is gorgeous.  Boxwood has great wine with a pristine layout.

Boxwood Winery Estates
Boxwood Estate Winery
Boxwood Winery Estates
Boxwood Estate Winery
Boxwood Winery Estates
Boxwood Estate Winery

After Boxwood, you jump back on US 50  and bike through the town of Middleburg. We had been here before years ago on a motorcycle and remembered the plethora of restaurants and cool shops in the downtown area.  This area is  a go to weekend stop for washingtonians. From antique stores to a conglomerate of restaurants and coffee shops, Middleburg is a great place to poke around on a lazy Sunday afternoon.

Yepp Child Seat
Yepp Child Seat

When we got back to Greenhill we pulled the bikes up to a table at the edge of the field and shared a glass of red wine. The little lady of ours scooted around on her Strider in the field and stomped through the very small snow pile that was rapidly melting.  We ran in the field chasing puppies and tried to catch the horseback rider on the horizon.

Crafted
Crafted — Haymarket, VA
Crafted
Crafted — Haymarket, VA
Crafted
Crafted — Haymarket, VA
Crafted
Crafted — Haymarket, VA

After a day of biking,  we loaded up the UAV and started the drive home making sure to stop at Crafted on the way back. The quaint shop was loaded with tons of craft beers, wines and ciders. The owners and their cheerful dog greeted us with a friendly smile and a nice chat about ciders and the awesome assortment of beers available!  The owners have an extensive knowledge about the 100s of beers stocking the shelfs and are more than willing to explain the differences of them all.   After purchasing a good amount of cider and beer for future samplings, we were on our way home wrapping up another awesome adventure.

Relaxing after a fun day!
Relaxing after a fun day!

4 Replies to “How to bike and wine taste as a family in Middleburg, VA”

  1. It seems like you’ve had a great week-end and you all enjoyed yourselves! I wouldn’t have thought of wine tasting as a family activity, but it’s nice to see there are creative families out there! Well-done!

    1. Thank you Irene! We don’t go many places without all three of us! She loves the bike and so do we! CHEERS!

  2. […] are not apposed to wine tasting with our little one, but on a Thursday afternoon the local wineries were not open since its the off season. So we […]

  3. I like that you have a united family and enjoy each other. Spending time with your family is the most beautiful thing. I hope you’ll keep doing such activities and telling us about them so that we can do such activities. Thank you and I wish you a good day!

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