Imagine the fictional Stars Hollow, but instead of an inn, Lorelai Gilmore runs an upscale dairy farm-turned-museum that dates back to the mid-19th century. There, you're in Woodstock. In fact, this charming oasis at the foot of the Green Mountains is so picture-perfect, the town buried its telephone wires to attract more Hollywood productions (you might recognize locations around town from Forrest Gump). Take your obligatory snapshots at one of the city’s historic covered bridges, eat fresh pie at the Woodstock Farmers Market, and visit the historic Marsh-Billings-Rockefeller Mansion. Then meander to one of the other adorable towns in the Upper Valley -- Barnard boasts a general store dating to 1832 and a fun summer farmers market with live music every Thursday night. -- T.S.
We see you, Charlottesville. But in the foothills of the Shenandoahs, no-stoplights Sperryville is as quaint as they come. Plan to stay at Hopkins Ordinary Bed & Breakfast, a B&B with an on-site brewery, one of several sources of top-notch brews. Pen Druid is a wild new fermentation brewery famous for Golden Swan, made from wild yeast strains found in Sperryville’s wildflowers. Locals opt for Rudy's Pizza or farm-fresh sandwiches at Before & After, but just up the road in Washington is the two-Michelin-starred The Inn at Little Washington. Diners book months in advance and come from near and far to try chef Patrick O'Connell's menu. Just make sure to get to bed early -- Old Rag Mountain beckons. This 9-mile hike is a safe bet for some mind-alerting views, especially at sunrise, when you’ll find few other hikers on the trail. --T.E.
Obligatory shout-out to trendy college town Bellingham in the north and Bavarian-themed Leavenworth in the mountains. But for a combo of breathtaking waterfront scenery, first-rate food, and loads of great watering holes, Edmonds gets our vote. Known to many Seattleites as simply “that place to get the ferry,” Edmonds has grown into a destination town in its own right, with spots like Salt & Iron and Bar Dojo anchoring a downtown long on big-city-worthy dining options. Enjoy a summer sunset over Puget Sound with a cocktail at Rory’s, or sip a famous northwest latte at Walnut Street Coffee. And outside Seattle, the state might not have a finer performing arts center than the Edmonds Center, which hosts theater and ballet all year long. -- M.M.
West Virginia: Morgantown
No small town in WVA is more worthy of a visit than the home of West Virginia University. Game days in Mo-Town are no joke, and the bar scene here rivals any major-conference college town. Suds and sports aside, Morgantown sits near the Cheat River, one of the premiere whitewater destinations in America. And a hike to the top of Coopers Rock gives you a jaw-dropping, vertigo-inducing peek into the 1,200ft gorge below. -- M.M.
Wisconsin: Eau Claire
It's a hair over our 60k population cap, but Eau Claire is still one hell of a spot to spend a low-key weekend. Bon Iver frontman and Eau Claire native Justin Vernon chose this city to set up camp for the Eaux Claires Music Festival -- head there in June to see the likes of Feist, Wilco, and Chance the Rapper. Two hip boutique hotels just opened downtown, our favorite being the The Oxbow, with locally sourced grub at The Lakely, a stage, and an art gallery -- plus, every room has a phonograph with free vinyl records to rent at the front desk. But don’t hole up in your room. Surrounded by lush farmlands, Eau Claire earned its name for its crystal-clear waters, so take advantage of the stunning river trails and over 1,000 acres of parks. At the relatively new Phoenix Park, you can hit the farmers market, then cross the river to Lazy Monk Brewing for craft beer flights (the rye IPA is awesome). -- D.N. and Josh Mellin, Thrillist contributor