As the leaves pile up on the sidewalks and the evenings get cooler, the familiar feeling of the year winding down begins. But this quiet period is often just the "calm before the storm." The upcoming holiday season is already starting to fill up our calendars, promising a joyful but demanding schedule of dinners, shopping trips, and celebrations.

Before every weekend is spoken for, why not intentionally carve out a little time for yourself? A simple overnight or weekend escape can work wonders. It's the perfect way to disconnect from the daily grind, reconnect with yourself or a loved one, and enjoy the peaceful beauty of autumn before the holiday rush truly begins.

To inspire your pre-holiday pause, we’ve gathered a few truly special destinations. These charming towns and serene retreats are all within easy reach of the DC area, offering the perfect setting for a quick, rejuvenating escape before your calendar fills up.

1. Historic Charm in Harpers Ferry, West Virginia (Approx. 1.5 hours from DC)

For a trip that combines stunning natural beauty with a step back in time, Harpers Ferry is ideal. As detailed by Secret DC, this charming town is located right in a National Historic Park, and early November is a perfect, crowd-free time to visit. You can take in the last of the fall foliage on a guided hike, explore history, and enjoy the stunning natural sights where the Potomac and Shenandoah rivers meet. As the nights get longer, the town's famous Ghost Tours run nightly, offering a spooky and historic layer to your evening. For a cozy indoor activity, you can also browse the Holiday Handmade Market (Nov 1 & 15) in nearby Shepherdstown or grab a drink at a History on Tap talk (like "Spies of Harpers Ferry" on Nov 20) at a local ale house.

To match the town's historic charm, look for cozy bed-and-breakfasts right in the historic district. Top-rated spots include the Light Horse Inn (dating back to the 1770s), which offers a stay steeped in history, and The Town's Inn, which places you just steps away from the national park's trails, shops, and tour starting points.


2. Luxury & Wine in Middleburg, Virginia (Approx. 1 hour from DC)


For a trip that blends rustic hunt-country scenery with world-class luxury, Middleburg is the perfect escape. Hailed as the nation's "Horse and Hunt Capital," the town is surrounded by rolling hills, picturesque horse farms, and low stone walls. As Secret DC points out, it’s an ideal escape for those looking to unwind, and Arlington Magazine highlights its "cozy inns." In early November, you can find unique experiences like a Full Moon Zip Tour (Nov 5) at the Salamander resort or cozy, hands-on cooking classes, such as a Fall Pies demo (Nov 15). Of course, you can always explore more than 20 local wineries (like Boxwood or Cana Vineyards), browse the antique shops on Washington Street, or visit the National Sporting Library & Museum.

To match the town's upscale yet cozy charm, you can indulge in a full-service resort or a historic inn. The Salamander Middleburg is a world-class destination for a truly luxurious escape, complete with an equestrian center and many of the aforementioned activities. For exquisite historic character, the Goodstone Inn & Restaurant offers a romantic stay on a 265-acre estate—and even hosts special culinary events like the Willowcroft Farm Wine Dinner (Nov 13). Finally, The Red Fox Inn & Tavern (one of the oldest inns in the country) places you right in the heart of the historic village.

3. Cider & Scenery in Charlottesville, Virginia (Approx. 2.5 hours from DC)

If your idea of a fall getaway involves scenic hikes and cozy sips, head to Charlottesville. As Arlington Magazine points out, it's a "pretty destination" for fall, and local hotels embrace the season with offerings like hot apple cider and curated hiking maps. The region is famous for the Monticello Wine Trail, and early November is packed with events. You can catch live music at the historic Jefferson Theater on the historic downtown mall. For wine lovers, the Two Up Wine Down festival (Nov 15) celebrates Virginia wine curators at the Jefferson School City Center, or you can explore ongoing events at Thomas Jefferson's Monticello, like their Culinary Conversations (Nov 13).

To complete the experience, the city offers a range of accommodations. Arlington Magazine highlighted The Forum Hotel for its modern comfort and seasonal packages. For other top-rated stays, consider the chic and artsy The Doyal Hotel, located on the Downtown Mall. For a full luxury resort experience, Keswick Hall (a Wardman Residential at Compass favorite!) is just outside of town, and for a charming boutique feel, the Oakhurst Inn is perfectly situated near the university.


4. Waterfront Serenity in Easton, Maryland (Approx. 1.5 hours from DC)


For a peaceful escape that combines colonial charm with the unique culture of the Eastern Shore, Easton is a perfect choice. This historic town serves as a sophisticated hub for art and cuisine, with brick-lined streets full of boutiques, galleries, and award-winning restaurants. As Arlington Magazine notes, it's a "pretty destination" with proximity to the arts and culture of nearby St. Michaels. The biggest event of the season is the Waterfowl Festival (Nov 14-16), a massive, town-wide celebration of wildlife art, decoy carving, and Eastern Shore heritage. If you're visiting earlier in the month, you can still catch the First Friday Gallery Walk (Nov 7), explore the Academy Art Museum, or enjoy the year-round Easton Farmers Market on Saturday morning.

To match the town's blend of history and waterfront relaxation, you have several excellent lodging choices. For a serene, quiet escape right on the water, The Oaks Waterfront Hotel (Arlington Magazine's pick) offers beautifully renovated rooms and private cottages. If you prefer to be in the center of the action, the historic Tidewater Inn is a beloved landmark that anchors the charming downtown, putting you within walking distance of all the shops, restaurants, and Waterfowl Festival exhibits. For a more intimate B&B experience, the Hummingbird Inn is a stunning Victorian mansion, also in the historic district.

No matter where you choose to go—a historic street in Harpers Ferry, a cozy inn in Middleburg, or a waterfront café in Easton—we hope you find a moment of peace. Taking a brief, relaxing getaway now is the perfect way to recharge your batteries before the holiday rush begins.

We'd love to see your fall adventures! Tag @wardmanre in your favorite photos from the charming towns and scenic backroads.


Book a call with our team!