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The Best Places to Enjoy Fall in and near Winchester VA!
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items After living in Winchester for over a decade, I can honestly say Fall was such a beautiful season to take in all of the sights and surroundings! Winchester and the surrounding area is the perfect mix of small town meets big city! Close enough to DC a...
My absolute favorite farmers market around Winchester! So much fun with kids, they have an awesome playground. Apple picking, hay rides, pumpkins, so much to do! Oh and their baked goods! Apple cider donuts freshly made here! Obsessed.
Marker Miller Orchards
So beautiful in any season but the gardens in the fall are magical! It’s so worth exploring both the museum and gardens on a beautiful fall day in the Shenandoah Valley!
Museum of the Shenandoah Valley | WIth acres of gardens, landscape and trails in Winchester, VA, the MSV preserves and enriches cultural life and heritage of the Valley
Old Town is so beautiful with its brick road and restaurants and shops! Our favorite thing to do is stroll along and go in and out of shops before deciding on a place to eat! El Centro is our favorite and it’s right in the center of the old town mall...
Old Town Winchester - Winchester-Frederick County Convention & Visitors Bureau
The views! The slower paced drive, the overlooks and hikes! So much to do and see here. Just a little ways down the road from Winchester is the start of Skyline Drive. It’s the prettiest thing I’ve ever seen in the fall, hands down!
Driving Skyline Drive - Shenandoah National Park (U.S. National Park Service)
Just outside of Winchester is the state Arboretum of Virginia and my oh my is it beautiful! It is so worth driving here and spending a few hours walking around and exploring the grounds, especially in the fall! We’ve taken our dog here so many times ...
State Arboretum of Virginia
The Apple Harvest Festival! With so many Apple orchards surrounding Winchester, a harvest festival just makes sense! It’s just like a hallmark movie with an Apple pie baking contest, arts and crafts, and tons of activities for the kids!
Shenandoah Valley Apple Harvest Festival
This farmers market is another must visit for us in the fall! So many pumpkins, they make a little (short) walking path to walk along while picking them out! They also have pies and apple cider donuts and other treats made fresh! Plus the produce for...
Virginia Farm Market
If you’re a lover of history and historical sites and homes, check out the Five Museums to experience through the historical society!! So worth exploring!
Home
About 20 minutes outside of Winchester; my husband and I stumbled upon this mill when they first started their fall art show. It is so worth a visit! It has grown so much with artists from all over the mid Atlantic region and the artwork is truly ama...
Mill
A beautiful golf course right on the edge of Winchester! The pictures are amazing but it’s even better in person. I know many families who are members there.
Home - Rock Harbor Golf Course - Rock Course
The family drive in! I just love that this still exists! So many movies watched under the stars here. Truly a gem in the area!
Home — Family Drive-In Theatre
If you’re into civil war history this is such an important place to visit. Not only for the role it played, but also in remembrance of the lives lost here. It’s beautiful here, with a wonderfully kept trail, and heartbreaking to think of what occurre...
Third Winchester Battlefield Park — Shenandoah Valley Battlefields National Historic District
Open through the end of October for its regular season, a visit to the Patsy Cline Historic House is a must downtown!
Visit | Celebrating Patsy Cline, Inc.
The Cedar Creek Battlefield is another place to visit in the area with either a self guided or ranger guided tours. Another Beautiful place, it’s so sad to think of what occurred there.
Tour Cedar Creek Battlefield (U.S. National Park Service)