B&B Highlights: Maryland and Virginia


A distinct briskness has crept into the air of late, and with a subtle turning of the leaves, fall casually makes itself known. For some, this is a signal to retreat indoors, to find a refuge from untimely nightfall and the evening chill. For others, now is the perfect time to revel in the seasonal metamorphosis. Fall represents a change of pace and a chance to experience Mother Nature’s milder mood.

Fortunately, a myriad of bed and breakfasts within reasonable driving distance of the District serve as perfect destinations for an autumnal excursion. Maryland and Virginia are home to some of the country’s most historic inns and the most beautiful backdrops from which to admire the fall foliage. Given that this year’s seasonal transformation promises to be fleeting, these locations offer a golden opportunity to take in what autumn has to offer.

Annapolis, Central Maryland

A mere 28 miles east of D.C., Annapolis offers a picturesque portrait of fall, and the colonial charm of its historic district is the number one reason to visit. The William Paca House and Garden provide a glimpse of 18th-century elegance. Additionally, the Hammond-Harwood House will hold its annual Children’s Pumpkin Walk on October 29. Tickets are available for a candlelight tour of Annapolis’ premier private residences on November 5 and 6, and while the weather is still warm enough, 74-foot schooners can be privately chartered. Around Church Circle, shopping and fine dining opportunities abound.

Church Circle is also home to Annapolis’ oldest tavern, Reynolds Tavern. Erected in 1737, the restored building is a stunning example of Georgian-style architecture. Reynolds Tavern features three luxurious suites, al fresco dining, English afternoon tea, and the Sly Fox Pub in its cellar. In the pub, formed of the original kitchen and foundation of the tavern, you can take your pick from 20-ounce beers and specialty drinks at Happy Hour. Reynolds holds its place at the top of many wonderful, quaint bed and breakfasts from which to enjoy fall in Annapolis.

Middleburg Northern Virginia

Middleburg is burrowed in the heart of horse, antique, and wine country. Local stables like Quanbeck Lane will take interested parties pleasure riding out on trails that wind their way through the foothills of the Blue Ridge Mountains. For the history buff, the Manassas National Battlefield and Bull Run Parks are close by, and antique-lovers will enjoy perusing shops in Middleburg, Leesburg, Purcellville, and Waterford. And of course, some of Virginia’s best wineries can be found in Middleburg, including Boxwood Winery, Chrysalis Vineyards, and Swedenburg Estate Vinyard.

Briar Patch Bed & Breakfast Inn serves as the ideal base of operations for an autumn exploration
of Middleburg. Constructed in 1805, the historic farm rests on an expanse of 47 acres. The inn itself has eight bedrooms available in the main house and a private cottage out back. Visitors will find horses grazing in Briar Patch’s fields and a porch overlooking the majestic Bull Run Mountain. Culinary options are also bountiful in Middleburg—you can take a weekend cooking class or head out to one of the area’s fabulous restaurants.

Front Royal, Shenendoah Valley

From strolling and shopping along downtown Main Street to hiking the Appalachian Trail, Front Royal offers an array of activities to appreciate the fall. The awe-inspiring Skyline Caverns are a scenic drive away, and you’ll find history everywhere, from the Belle Grove Plantation to the Confederate Museum. Much like Middleburg, wineries and antique shops abound.

Dorastus Cone built his home in 1869 and called it Lackawanna, which means “meeting of the waters” in the language of the Delaware Indians. Aptly named, the Italian-style residence lies between the north and south forks of the Shenandoah River. Today, Lackawanna is a stately, spacious bed and breakfast, with waterfront views and three rooms to choose from. Guests have access to local fishing and canoeing sites, as well as a plethora of hiking and cycling paths to explore. Several nearby golf courses allow visitors to appreciate the coming of fall while getting in a round or two. For the full, fall outdoor experience, bed and breakfasts in the valley can’t be beat.

Charlottesville, Central Virginia

Charlottesville remains a hotspot for those who frequent bed and breakfasts, no matter what the season. When it comes to getting a taste of the 18th century, few places can immerse visitors more than Prospect Hill Plantation Inn & Restaurant. The 1732 manor house remains intact, as do its seven original dependencies and slave quarters. Inn offerings include thirteen fireplace rooms, two candlelit dining rooms, 50 acres of sprawling fields and woodlands, and quick access to historic sites like Monticello, which is just down the road. Most importantly, the bed and breakfast features a 5-acre arboretum that holds the rarest magnolia in the United States. Prospect Hill affords guests a one-of-a-kind front row seat to the changing of the season, and it does so in style.

For those who prefer downtown Charlottesville, The Dinsmore House Bed & Breakfast is conveniently situated on “The Corner”. The Dinsmore has the distinction of being built by Thomas Jefferson’s master builder in 1817. Furthermore, the bed and breakfast has seven bedrooms with private bath and offers homemade breakfasts and afternoon social hours. Being centrally located on the University of Virginia campus, many restaurants and shops are within easy walking distance. Only a short drive from Skyline Drive, The Dinsmore still grants visitors the liberty to throw themselves headlong into fall.

Williamsburg, Tidewater

Few cities take advantage of fall like Williamsburg. By day, horse-drawn carriages saunter up and down Duke of Gloucester Street, showing off spectacular views of fall in Colonial Williamsburg. At night, lantern-lit ghost tours draw screams from nervous participants, and witch trial reenactments are held in the Capital Building. Aside from these curiosities, Williamsburg Marketplace provides a complete shopping experience, and taverns serving authentic colonial cuisine line the streets. Christiana Campbell’s and King’s Arms Tavern are tourists’ favorites, but more traditional restaurants of choice include the Fat Canary and The Trellis.

While there are a number of bed and breakfasts in the area, the 1904 A Williamsburg White House Inn is the oldest. Offering an Autumn Getaway package, the White House features decadent suites, lush lawns, and a serene garden. Conveniently located within walking distance of Williamsburg’s highlight attractions, the Inn is a romantic setting in which to welcome autumn.

Washington residents have a variety of options when it comes to fall travel. From the colonial environment of Williamsburg to the bucolic feel of Middleburg, each place has a character all its own. Bed and breakfasts have a way of bottling their locale’s essence. All it takes is finding the one that piques your interests and heading out on the tree-lined road to get there. A visit to any of these remarkable destinations will make this autumn unforgettable.

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