Follow the Apple Trail this Fall in Winchester

Frederick County invites you to plan your getaway around one of the many fall festivals for a true Winchester experience.

Day 1:

Make the Winchester-Frederick County Visitor Center and Civil War Orientation Center your first stop. We will be happy to help you plan your day! Start by watching our eight minute video about Winchester-Frederick County.

Before departing our parking lot, be sure to visit Winchester’s oldest home, Abram’s Delight Museum. The tour includes the 1754 limestone house, and the 1797 log cabin. A tour of this complex is a great way to learn about the first settlers to our area.

At the Old Town Pedestrian Mall, you'll find unique places offering something for everyone.

Enjoy lunch at one of our outdoor cafes or sit at the same lunch counter as Winchester native and country music legend, Patsy Cline, at the Snow White Grill. After lunch, pick some of Winchester's notable apples (and some of Virginia’s finest, we might add) at the different markets you'll encounter.

A stop at Marker-Miller Orchards is a must and their apple cider doughnuts are the best. It’s not just the apple doughnuts though that makes this orchard memorable, it’s also the scenic views of the orchard, the mountain vistas, and the cool mountain breezes. Enjoy all this from a front porch rocking chair.

Got ghosts? We do! And after dinner, explore Historic Jordan Springs on one of their paranormal investigations! This historic setting was once a resort known for its healing springs.

Rest up at the Hilton Garden Inn, be close to apple country at the Courtyard by Marriott, or stay right in Old Town at The George Washington Hotel, a restored Wyndham Historic Hotel.

Day 2:

Begin your day at the Museum of the Shenandoah Valley. Visit the five-gallery museum, spectacular 6-acre gardens, and the historic house. Allow three hours for your visit and then enjoy lunch and shopping at Creekside Station. You’ll want to take home handcrafted soaps from the Lavender Moon Soap Company and yummy chocolate from Shenandoah Fine Chocolates.  It will be a sweet way to wrap up your day.

A scenic drive to Middletown will lead you to historic Belle Grove Plantation. This 1797 manor home offers breathtaking mountain views. Go back into time as you learn what life was like at the home during the time of the Battle of Cedar Creek, which raged all around the home.

Enjoy dinner in a historic bank building at Nana's Irish Pub in Middletown. Co-owner Brian Coughlin will entertain you with traditional Irish songs and guitar playing.

Day 3:

Venture to GNC Antiques for some antique browsing. Forty dealers are showcased in 10,000 square feet. Find pre-owned, quality Henkel-Harris furniture - made in Winchester! GNC is located in Old Town.

Last night was Irish, so today for lunch, try English; an English pub, that is!  The Union Jack is located on the pedestrian mall and offers the traditional fish-n-chips, a must for the hungry shopper! Enjoy an afternoon among the grapes and vines at Veramar Vineyard. You’ll marvel at the views and enjoy the hospitality of the Bogaty family. Cheers!

The Winchester-Frederick County Convention & Visitors Bureau invites you to partake of this fall tour. See autumn splendor at its best. Visit apple country; Winchester-Frederick County, Virginia!


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