As the pandemic continues to evolve, please check with venues before you go and stay up to date on current COVID-19 protocols.
An Artisan Shopping Trip
Indianapolis • Drive time: 3 hours ■ ■ ■
When the swanky Bottleworks Hotel (from $249; bottleworkshotel.com) opened last December in Indy’s old Coca-Cola plant, it sparked a boom in its 12-acre Bottleworks District. Make a beeline to Good Neighbor for stylish and responsibly made clothing brands, Pumkinfish for stocking stuffers, and Woodhouse Day Spa for its salt therapy room. Later, sip an Old Pretender with fig-infused Scotch at the new apothecary-themed Sundry and Vice before an indie flick at the eight-screen Living Room Theaters.
Extra: Continue on Indy’s buzzy Massachusetts Avenue for more options, including FortyFive Degrees, a sushi bar with a window made for people-watching, and College Avenue’s Penn & Beech Candle Co.
A Romantic Culinary Affair
Galena, Illinois • Drive time: 3 hours ■ ■ ■ ■ ■ ■
Once upon a time, beef Wellington was the reason to dine at the Goldmoor Inn (from $305; goldmoor.com), an elegant B&B overlooking the Mississippi River. Now there’s another: new executive chef Brandon Veitch (formerly of the Lobby at the Peninsula Chicago), who’s whipping up dishes like slow-braised short ribs with shaved black truffles. Afterward, get comfy in your choice of 13 suites, three cottages, and two log cabins (one that’s pet friendly). The cabins are especially secluded and winning in wintertime, if only for the breakfast delivered to your door.
Extra: December in Galena is a festive affair, so take in any number of cheery events, including Classical Blast’s Dark Side of the Yule concert (December 10); Night of the Luminaria, featuring a candlelit classical music concert (December 11); and the Goldmoor’s seven-course New Year’s Eve menu.
A Woodland Retreat for Grownups
Kohler, Wisconsin • Drive time: 2 hours 25 minutes ■ ■ ■ ■ ■
You’ve heard about the resort’s over-the-top spa and championship golf courses, but recent additions are turning Destination Kohler (destinationkohler.com) into an unexpected all-seasons gem. Hotel accommodations include the American Club (from $191), but a dreamy itinerary for couples or adult groups starts with one of four super-luxe two- to four-bedroom cabins in the woods — or on a pond or Lake Michigan — each outfitted to the nines with full kitchens (from $1,029). From there, plan on ice bowling and snowshoeing at the 500-acre River Wildlife, a proper spa day (duh), and private dome dining at the Taverne on Woodlake.
Extra: Meander the free new Art Preserve near Kohler. The museum’s exterior is a striking mix of concrete and soaring timbers; the unique artist-built environments inside were all created using found objects.
A Sleepaway Camp With Your Dog
Lake Delton, Wisconsin • Drive time: 3 hours ■ ■ ■ ■
The perfect holiday gift for you and your pooch: winter camp at Camp Dogwood (January 7–9, $495 per human for up to two dogs, campdogwood.com), a lakefront camp set on 700 acres. The price includes your own room and bathroom, all meals, and a slew of indoor and outdoor events geared toward both newbies and pros in the world of organized dog activities. Each day, choose from barn hunts, canine circus school, sheep herding, pet projects (read: arts and crafts), pack walks through the woods, and as many naps as you like. At night, guitar music and a big campfire are the backdrop for a Champagne toast under the stars.
Extra: Not a dry eye will be found when dog sledding begins and every pup — from blind dogs to tiny Cavaliers — has its day.
A Snow-Packed Family Adventure
Lake Geneva, Wisconsin • Drive time: 1 hour 30 minutes ■ ■ ■ ■ ■
Give in to the first snowfalls of the season with a spontaneous trip to Grand Geneva Resort & Spa (grandgeneva.com). Take your pick of anything from skating and sledding to snowshoeing to a perfect 20-run hill for ski and snowboard lessons. Sip hot chocolate inside the new club lounge while warming your bum by the fire, or go for a jaunt to the nearby Timber Ridge Lodge & Waterpark.
Extra: You could have groceries delivered and make dinner in your modern villa (from $50), but then you couldn’t stuff your face in a private igloo with a well-earned dry-aged steak from Geneva ChopHouse, which has a new heated patio.
An Instant Escape at a Luxe Inn
Lake Forest, Illinois • Drive time: 35 minutes ■ ■ ■ ■
Expect to be enamored with the 57-room Deer Path Inn (thedeerpathinn.com), a hop-skip from the city but seemingly worlds away. Step up to a wooden reception desk backed by a wall of room keys, and the high-touch service will whisk you to posh rooms with Frette linens and massive suites with tubs filled by a ceiling waterfall. Then warm up with a glass of Cabernet by the fireplace, all part of the charm of this English manor–inspired hotel. Dinner reservations are coveted, so get yours in advance for the Bar, English Room, and brunch on the heated courtyard patio (a beauty even in winter). Steps away, find bougie boutiques.
Extra: The Deer Path Inn is as fancy as it is playful. Think private mixology classes in a cellar, outrageous holiday cocktails, festive packages for grandparents, and one of the most entertaining, binge-worthy hotel Instagram feeds we’ve seen (@deerpathinn).