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Bloomington, Indiana | Quechee and Woodstock, Vermont | Santa Fe, New Mexico | Ann Arbor, Michigan | Decorah, Iowa | Red Lodge, Montana | Leavenworth, Washington | Midway, Utah | New Hope, Pennsylvania | Syracuse, New York | Cape May, New Jersey | Lake Geneva, Wisconsin | Ashland, Oregon | Lake Placid, New York | Nevada City, California
While the rising cost of travel continues to be a concern, the number of adults age 50-plus expecting to take a trip in the near future is on the rise, according to a recent AARP Travel Trends survey. The majority acknowledge their primary motivations, including mental and physical well-being, are spending time with family or friends, escaping everyday life and finding time to relax and rejuvenate. The survey also confirms that spring and summer remain the most popular times for domestic trips, but winter holds appeal for travelers seeking to find new cold-weather getaways.
With this in mind, we’ve plucked 15 of our favorite chilled-out (literally) domestic destinations that ratchet up hibernal merriment and deliver snow globe charm. While some people might prefer beach vacations when the mercury drops, we’re pretty sure you’ll enjoy the holiday glitter, icy outdoors and seasonal community events these towns deliver. Note: Pricing is accurate at the time of publication.
Bloomington, Indiana
Snowy rolling hills and ice-covered trees transform Bloomington into an urban winter wonderland, especially around downtown’s light-strung square and historic Monroe County Courthouse. Wander down iconic Kirkwood Avenue, chock-full of shops, cafés, bars, restaurants and performance venues. Indiana University’s walkable, 1,900-acre campus is nearby, too, and home to one of B-town’s hidden gems: the world’s largest collection of mechanical puzzles — more than 35,000 of them — tucked inside IU’s Lilly Library. Of course, no college town is complete without a good watering hole, and Crazy Horse is a local favorite thanks to cheap daily specials, including $5 Mule Monday, Tequila Tuesday and Whiskey Wednesday and $4 mimosas and Bloody Marys on weekends. Get your live music fix at the famed Bluebird Nightclub, where tickets run between $14.25 and $28.
If you prefer to immerse yourself in serene winter scenery, the Griffy Lake Nature Preserve has a half dozen trails for every hiker level, according to AllTrails. Ice-carving competitions, kids’ games and a chili cook-off are in store for visitors to the free Freezefest, which will take place at Switchyard Park from Jan. 23 to 24, 2026.
Stay: Showers Inn, within walking distance of Kirkwood Avenue, has 12 cozy rooms, some with fireplaces, plus free parking and daily breakfast. Rates start at around $139.
Quechee and Woodstock, Vermont
Just two and a half hours from downtown Boston, these two historic villages, less than 8 miles apart, deliver double the opportunity to experience picturesque New England charm. Stroll hand in hand along Woodstock’s Central Street, lined with clothing boutiques, art galleries and the Yankee Bookshop, where you can pick up a bestseller or browse the selection of vinyl records. On nearby Elm Street, family-owned F.H. Gillingham & Sons General Store has shelves full of locally made Vermont goodies, including cheddar cheese and maple syrup.
One of Vermont’s best-kept ski secrets is Ski Quechee, a forgiving family-friendly hill with full-day lift tickets for just $62 and half-day tickets (after noon) for $48 ($25 if you ski from 2-4 p.m. on Fridays to Sundays). Ten minutes from the village of Quechee is the Simon Pearce Factory Store, where visitors can watch glassblowing demonstrations or shop for finished goods and holiday decor at the flagship store in Quechee, where there’s also a restaurant overlooking the Ottauquechee River. Before heading home, make sure to snap a photo of the area’s picturesque covered bridges.
Stay: The seven rooms at the adorable Village Inn of Woodstock are full of antiques, and a second-floor suite has an original woodburning fireplace. Best of all, a gourmet breakfast made with Vermont ingredients is included with the stay. Rates start at around $279 Sunday through Thursday.
Santa Fe, New Mexico
Though the Southwest conjures images of scorching heat, Santa Fe, with its year-round sunshine and 7,198-foot elevation, is a winter paradise from about November through March, with an average of 32 inches of snow in town and up to 300 inches in the surrounding mountains. Skiing is a popular pursuit, since you can be schussing down the slopes just 35 minutes from downtown at family-friendly Ski Santa Fe, where weekday full-day lift tickets for older adults (ages 62 to 71) are $84 ($22 for those 72-plus).
Take a wintry stroll along Canyon Road, a pedestrian-friendly stretch of former adobe homes that now house varied Santa Fe art galleries. Take a two-hour Sense of Place Walking Tour of the nation’s oldest and highest capital city, offered daily at 10 a.m. for $30 per person. For a taste of some of Santa Fe’s stellar cuisine — and some dining-out deals — visit during Santa Fe Restaurant Week, taking place March 2–11, 2026.
Stay: Around a mile from Santa Fe’s famed plaza, the 154-room Sage Hotel is a pet-friendly option, with complimentary amenities including a downtown shuttle, breakfast, guest laundry and Wi-Fi. Winter midweek rates start around $70.
Ann Arbor, Michigan
The city of Ann Arbor, about 45 minutes west of downtown Detroit, is home to the University of Michigan, which means there is usually a lot going on — and not just on game day. There are several free museums on campus, including the University of Michigan Museum of Art, which houses a large collection of European, Asian, African and American art and hosts dozens of special exhibitions each year. Car buffs should motor 8 miles east to the Ypsilanti Automotive Heritage Museum, spotlighting Michigan’s auto-manufacturing history with displays of vintage vehicles ($5 admission).
Looking for some winter retail therapy? Ann Arbor’s downtown is made for shopping, walking, browsing and eating, thanks to its abundance of stores, independent theaters, bars, breweries and restaurants (Main, State and Liberty streets are good places to start). Take a quick stroll through the Nickels Arcade, a covered shopping corridor listed on the National Register of Historic Places, and check out the calendar of events at Literati Bookstore and at the Michigan Theater, which hosts some free events.
At most downtown bars, you can count on daily food and drink discounts. Drop by for Tuesday night bingo, Wednesday trivia night and $7 build-your-own burgers on Thursdays at Good Time Charley’s. Locals don’t let a little cold weather stop them from enjoying the numerous surrounding parks all year long, and you shouldn’t, either. Top among cross-country skiers and snowshoers is 439-acre Rolling Hills County Park, where the varied terrain and trails suit all levels. You can rent skis and tubes for $10 an hour.
Stay: In the heart of downtown (walkable to everything), the modern Exhibit A2 Boutique Hotel gives visitors a little more elbow room with nine apartment-style suites featuring in-unit kitchens, laundry machines and cozy seating areas. Sunday to Thursday rates average around $130.
Decorah, Iowa
In the northeast corner of the state in an area known as the Driftless (“a part of the country the glaciers missed,” according to Visit Decorah), this picturesque town of fewer than 8,000 people is just as beautiful in winter as it is in summer — though it requires a few more layers for an enjoyable stroll past the downtown district’s historic buildings on Main and Water streets that are home to restaurants, boutiques and bars. Decorah is also home to the country’s largest museum devoted to a single immigrant group, Vesterheim, The National Norwegian-American Museum and Folk Art School, which holds 33,000 artifacts, folk art, tools and furnishings ($15 admission, $13 for 65-plus but free on the second Saturday of the month).