October is one of the best months to explore the region we call home. From city streets and neighborhood markets to Virginia wine country and the shores of Southern Maryland, there are plenty of ways to spend a fall weekend. Whether you want to stay close to DC or take a scenic drive a little farther out, here are 10 things worth putting on your calendar before November.
1. Explore a DC Neighborhood You Don't Usually Visit
Skip the usual tourist stops and spend an afternoon exploring somewhere new — browse local shops, grab coffee, find a great restaurant, or simply wander.
2. Take a Scenic Drive Through Virginia Horse Country
Head to Fauquier County and explore the roads around Middleburg, The Plains, Warrenton, and Upperville. Think rolling farmland, horse country, historic properties, and plenty of opportunities to stop along the way.
3. Spend an Afternoon on the Waterfront
For a slower pace, head to Southern Maryland and enjoy the Chesapeake. Explore a waterfront town, grab local seafood, browse shops, or find a spot to watch the boats.
4. Explore Fredericksburg's Historic Side
Walk the streets of historic downtown Fredericksburg and mix history with shopping, galleries, coffee, and restaurants. It's an easy day trip that feels like a change of scenery without going too far.
5. Visit a Farmers Market Before the Season Winds Down
Pick up local produce, baked goods, flowers, or something you wouldn't normally find at the grocery store. Look beyond the big markets and discover one in a nearby community.
6. Go Apple Picking or Visit a Local Orchard
Make a day of it at an orchard in Northern Virginia or Maryland. Pick apples, grab some cider or baked goods, and enjoy the countryside while it's still comfortable enough to spend time outdoors.
7. Spend an Afternoon at a Winery, Brewery, or Cidery
October is a great excuse to explore Virginia's wine and craft beverage scene. Choose a scenic location, settle in for an afternoon, and make the destination as much of the experience as the drinks.
8. Explore Southern Maryland's History
Go beyond the waterfront and spend a day exploring the region's history, from historic sites and museums to colonial-era communities and places connected to Maryland's early history.
9. Take in the Fall Foliage on Foot
Trade the car for a trail and explore one of the region's parks or nature preserves. Whether it's a quick neighborhood walk or a longer hike, October is an ideal time to get outside.
10. Plan a “Yes, I've Never Been There” Day
Pick a town, neighborhood, restaurant, park, museum, or attraction you've driven past a dozen times but never actually visited. Put it on the calendar and make a day of discovering somewhere new.
If you’re looking for specific events, festivals, concerts, farms, and more, check out our list of favorite activities for fall and early winter here.
