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  • 1296 Clifton Inn Dr, Charlottesville, VA 22911, USA
    A year ago I had dinner at the Clifton, then under the supervision of Tucker Yoder. Mr. Yoder was elsewhere that evening, but I spent several hours at the “chef’s counter” in the kitchen, watching executive sous-chef Jarad Adams work his own delicious magic. Naturally Mr. Adams was meticulous with his food prep, but he was also surprisingly generous with his time for me. Imagine my delight when I returned this year to find Mr. Adams had been promoted to Executive Chef. On this visit, Mr. Adams’s tasting menu showed the same attention to detail as I remembered, but with a greater sense of adventure — even whimsy. From the amuse bouche (a spoonful of polenta topped with pork belly, apple, and a sprig of fennel) all the way through to the sticky toffee pudding with candied pecans, dates, and caramel ice cream for dessert, I was enchanted. The tasting menu consists of four courses and varies by the season. My first course was a toss-up between the butternut squash and apple soup and the shaved winter vegetable salad with hazelnuts, black cocoa, and a buttermilk dressing. I had no regrets about my choice of the salad, especially as butternut squash was the foundation of my next course: the most perfectly seared sea scallop I can remember. From there it was onto monkfish with beluga lentils, with Brussels sprout leaves dancing on top. Mr. Adams knows what he’s doing in the kitchen, and the Clifton — and Charlottesville — is lucky to have him.
  • 191 Chinquapin Dr, Waynesboro, VA 22980, USA
    The Iris Inn, a luxury Shenandoah bed and breakfast, is the perfect base to explore Virginia’s Blue Ridge mountains. Located 30 minutes from Charlottesville, the Inn is close to nearly 30 wineries and is within a few minutes drive to the southern entrance of Shenandoah National Park. Owners Dave and Heidi Lanford warmly welcome visitors to their cozy mountainside inn with gourmet breakfasts and a complimentary nightly happy hour. The eco-friendly B&B also offers an electric vehicle charging station.
  • 1435 Carters Mountain Trail
    Head five miles out of town for great scenery and a fun family outing. Pick your own seasonal fruits and vegetables (or buy them at the farm stand) and enjoy casual farm-to-table dining, Prince Michel, wines and Bold Rock hard cider—all with an impressive view. Thursday evenings until 9 p.m. from May through September feature dinner, live music, hayrides, and memorable sunsets. The Apple Harvest Celebration starts in September.
  • 200 Ednam Dr, Charlottesville, VA 22903, USA
    A bucolic resort in the Virginia Piedmont, the Boar’s Head Resort is as deeply rooted in Virginia as its owner and neighbor, the University of Virginia. The land has hosted travelers since 1759, with the original Birdwood mansion dating to 1830. A short drive from downtown Charlottesville, Boar’s Head has plenty to keep a visitor occupied without even leaving the property, including an 18-hole golf course, a full-service spa, a fitness center with squash and tennis courts, and three swimming pools. The resort has 175 rooms spread over 573 acres; suites feature a seating area and balcony or patio, and some have fireplaces. Dining options range from healthy café fare (necessary fuel for all those tennis matches), to a grill overlooking the golf green, to an elegant meal in the restored Old Mill Room. The Blue Ridge mountains are renowned for their fall foliage, but visit in summer for fewer crowds (and UVA students) and the English-inspired grounds and gardens in full bloom. Be sure to ask for details on arranging a hot-air balloon ride over the countryside to appreciate all of historic Virginia.
  • 701 Club Drive
    Keswick Hall was originally built in 1912 as a family estate and was later a country club before being transformed into a country hotel in the 1990s, and it continues to evolve as a luxury resort in its second century. Experience a bit of the historic grandeur with an elegant al fresco dinner overlooking the countryside at Fossett’s restaurant or with a cocktail at the Villa Crawford bar (named for the original home), before retiring to your room on a bed fit for royalty. (Indeed, the handmade Hypnos mattresses are also commissioned for the British royal family.) Each of the 48 uniquely designed rooms and suites overlook the golf course or gardens, and have minibars stocked with local goodies. You’ll need a good night’s sleep to properly enjoy a full day’s activities on property: a round of golf on the Pete Dye–designed Full Cry course, a tennis match on one of seven courts, or a game of croquet or horseshoes (just a few of the games on offer). Wind down with a massage, signature vinotherapy facial, or raindrop therapy with essential oils at the spa. If you can bear to leave the lush grounds, downtown Charlottesville and the Monticello estate are each a 15-minute drive away.