Frederick On The Road: Sperryville, VA

It all started with our one-year wedding trip for us, now we (Alanna and Cory) go back once or twice a year to relax and getaway for a quick re-charge.

Just under two hours from our homebase in Frederick, its the perfect overnight trip. What we like to do is take off on a Friday and head out around 10am to make it down for lunch around noon. While there are plenty of spots to stop, sip and eat, we save that for the trip back. When we get down at noon, we always drop the bags at our favorite bed & breakfast of all time - 'Hopkins Ordinary'. and walk striaght over to lunch at Headmasters Pub. Yes walk. Sperryville is super small (only 228 people live in sperryville) however its mighty in what it provides.

  • 2 breweries

  • Hopkins Ordinary Ale Works

  • Pen Druid

  • 1 distillery

  • Copper Fox Distillery - The craft cocktails at this place are incredible.

  • 3 Restaurants

  • '3 Blacksmiths' (3 Starred Michelin Rest. - If you're thinking of checking it out, take note they are booking about 8 months out.)

  • Headmasters Pub

  • Rappahannock Pizza Kitchen

  • 1 Coffee Shop

  • 1 Corner Store (Its adorable)

  • 1 Bed & Breakfast

What more could you ask for?

Okay back to the time line

Day 1

12:00pm - Lunch at Headmasters Pub

1:15pm - Whiskey Tasting and cocktails on the river at Copper Fox Distillery (You're Welcome)

3:30pm - Check in at Hopkins Ordinary (Freshen up from the day)

4:00pm - Enjoy amazing beers in the beer garden at Hopkins Ordinary or, take them up and sit on your private balcony with either rocking chairs, or porch swings (the choice is yours, both are nice.)

6:00pm - Freshen up for Dinner

6:30pm - Dinner at Rappahannock Pizza Kitchen on their private balcony with an outdoor bar. The pizza is not to be missed. It's incredible!

8:00pm - Pit stop at the corner store to grab a bottle (or two) of wine and cheese.

8:15pm - Sit outside in your rocking chair porch swing and enjoy each others company sipping fantastic local wine paired with good cheese. (SIGN ME UP!!)


Day 2

7:00am - Head downstairs w/ a book for some awesome coffee in a quiet cozy environment and sit outside on the front porch swing as this sleepy little town begins to wake up.

8:15am - Sit inside or out and enjoy some of Kevin's amazing breakfast. He pulls it off, every time!! (Picture below)

9:15am - Head back up, pack and freshen up, for the day is about to get even better!!

9:45am - Take a quick walk up the only road in town, grab another coffee or sweet treat at 'Before & After"

10:00am - Check out Happy Camper for some cool Hiking and Sperryville swag.

11:00am - Check out


11am-4pm - Take your time, stop and enjoy wineries on the trip back home. Seriously, you can throw a rock in any direction and hit a winery. There are some really good ones along the way. (Need any recommendations, reach out!) There you have it! A quick up and back to Sperryville VA. A true gem that everyone should experience. Another great thing about Hopkins Ordinary, no tv's in the bedroom and the service is spotty. Great way to disconnect and be present : )

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