Going Places: Cheeriest Places for Families to Celebrate the Winter Holidays

Favorite Destinations

Here are some of our favorite destinations to spend the holidays – because they are so festive, have so many activities and things to do:

Newport, R.I., which does the most fabulous “Christmas in Newport’ events each year, with the historic Newport Mansions decorated to the hilt and the delightful Cliff Walk, www.newportmansions.org, www.discovernewport.org, https://www.discovernewport.org/events/christmas-in-newport/)

Philadelphia offers an amazing array of magical light shows and activities. Winter at Dilworth Park around City Hall is where you find the Made in Philadelphia Holiday Market, Rothman Orthopaedics Ice Rink and Cabin, and Wintergarten on the Greenfield Lawn. Other holiday markets are at Peddler’s Village and Christmas Village. Dazzling activities include: LumiNature at the Philadelphia Zoo, the Holiday Light Show at Shady Brook Farm; the iconic Wanamaker Light Show & Dickens Village (thru Dec. 24); and  Miracle on South 13th Street Holiday Light Display (neighbors on the 1600 block of South 13th Street between Tasker Street and Morris Street in East Passyunk have worked together every year for over three decades to create elaborate presentations that adorn their neighborhood 5-10 pm nightly through January). Also: Wild Lights at the Elmwood Park Zoo, A Longwood Christmas at Longwood Gardens (Kennett Square, PA, thru Jan. 11), Holiday Garden Railway and Nighttime Express at Morris Arboretum & Gardens (thru Dec. 30). Independence Blue Cross RiverRink Winterfest on the Delaware River waterfront offers free skating (tickets required, pay-as-you-go games and amusement rides on the boardwalk,seasonal treats and hot drinks. Stay the night with the Visit Philly Overnight Package and score free hotel parking. More at https://www.visitphilly.com/holidays-in-philadelphia/.

Greater Wilmington, Delaware holiday events include Yuletide at Winterthur (Winterthur.org),  Holidays at Nemours Estate, A Longwood Christmas at Longwood Gardens,  Holidays at Hagley (hagley.org ), The Brandywine Railroad. (https://www.visitwilmingtonde.com/things-to-do/holiday-magic-in-greater-wilmington-delaware/)

Washington DC is one of my favorite places to spend the holidays: there is so much to do and see indoors when you want to get out of the cold, as well as wonderful reasons to be outside. Seasonal Theater: ho ho ho ha ha ha ha (thru Dec. 21: Woolly Mammoth Theatre); A Christmas Carol (thru Dec. 31, Ford’s Theatre); The Washington Ballet presents The Nutcracker (thru Dec. 28, DC-themed production at the Warner Theatre features dancing cherry blossoms, Harriet Tubman and George Washington); Dr. Seuss’ How the Grinch Stole Christmas! The Musical (Dec. 30-Jan. 4, 2026, National Theatre). Displays and Holiday Delights: Snowglow at the Dome at Hi-Lawn (thru Jan.4: a 50-foot heated rooftop dome atop Union Market hosts a visual and culinary holiday experience with state-of-the-art winter scenes projected overhead and festively decorated bars). DC Holiday Market (Dupont Circle, thru Dec. 23); DowntownDC Holiday Market (Penn Quarter, thru Dec. 23, with 115 local artisans); National Mistletoe (thru Dec. 23: aerial art installation by artist My Ly at Anthem Row); Winter Glow (select dates thru December: George Washington’s Mount Vernon is illuminated with brilliant lights set to holiday music.); Winter Wonderfest at Nationals Park (thru Dec. 24,  a winter wonderland with snow tubing, curling, kids’ activities and adults-only ski chalet); CityCenterDC’s Holiday Tree (thru early January: a 75-foot tree at the luxury shopping destination). Enjoy ice skating at The Wharf, Georgetown and Canal Park and Winter Skate at the National Building Museum, a special indoor skating experience in the museum’s Great Hall, Dec. 27-Feb. 8. Maximize the value of DC and plan your trip at washington.org/winter.

Fortunately, my favorite holiday destinations also have Historic Hotels of America members. I always seek members of Historic Hotels of America wherever I go, but especially at Christmas time because they never fail to make the holidays truly special. These hotels – so often known as “The…” – embody heritage, the character of the place and their walls seem to speak the stories of their past. Among our favorites for the holidays: The Sagamore on Lake George (skiing at Gore Mountain), Mohonk Mountain House (New Paltz, NY); the Red Lion (in Norman Rockwell-picturesque Stockbridge, MA, with skiing nearby at Jiminy Peak), Mountain Top Inn (Chittenden, Vt, near Killington);  Omni Mount Washington (Bretton Woods, NH, skiing at Bretton Woods), Woodstock Inn & Resort (Vermont, skiing at its own Saskadena Six Ski Area and cross-country on property). If you prefer Christmas in warm weather:  the Del Coronado (San Diego), the Chattanooga Choo Choo (TN), Jekyll Island (GA), Hermitage (Nashville), Union Station (Nashville), Heathman (Portland OR). And for a beach holiday with palm trees instead of pine: Vinoy  Golf Resort & Spa (St. Petersburg, FL), the Don Cesar (St Pete Beach, FL), Colony Hotel & Cabana Club (Delray Beach, FL). More ideas at historichotels.org.

Favorite Ways to Spend the Holidays

Ski holidays are so terrific to bring families and friends together –you come in from the cold and some adventure on the slopes to a cozy condo, sit before a fire, join in some lovely activity around a fire pit and talk about your narrow escapes on the mountain. We so enjoyed our holiday stay in Lake Placid in New York’s Adirondacks, affording a truly unique total Olympic experience skiing and an immensely charming village. There are several charming, historic places like the Mirror Lake Inn, Lake Placid Lodge, the Whiteface Lodge. High Peaks Resort and we thoroughly enjoyed our holiday stay at the Golden Arrow Lakeside Resort (www.golden-arrow.com).  (More ideas at lakeplacid.com and iskiny.com)

But if you are looking for a ski in/ski out ski resort some of our favorites include Stratton Mountain, (Manchester, Vt), Smugglers Notch and Okemo Mountain in Vermont (more ideas at skivermont.com). Longer haul, we love Palisades Tahoe and Heavenly in Lake Tahoe, Calif.; Keystone Resort, Winter Park, Copper Mountain (Colorado) for their vibe, activities and, of course, outstanding skiing for the family.

One we haven’t yet visited but have on the list as a must do is the Von Trapp Family Lodge & Resort  (yes, that Von Trapp Family – you can’t get more Christmas-y than that – is famous for cross-country skiing, and so much more).

Dude ranches are really fun for the whole family and do a fantastic job in the winter – many even have their own ski slopes or tubing hills. A favorite for generations is Rocking Horse Ranch Resort, Highland, NY (https://www.rockinghorseranch.com/).

Cruising is a great way for families to be together for the holidays. Royal Caribbean Cruise Line, Disney Cruise Line, Norwegian Cruise Line and Princess Cruises do a superb job for families, with spectacular entertainment, waterparks and other mind-blowing activities and entertainment on board and age-appropriate children’s activity programs and dining options. These floating resorts bring families together around activities and interests, dining and entertainment, adding in the incalculable delight of exploring new places. Our family treasures our multi-generational reunion on a Carnival cruise during Christmas week that called at Key West and Cozumel (Mexico), both such colorful places. Your travel agent can best advise on choosing a ship, a cruiseline, an itinerary; also visit cruisecritic.com.

Theme parks really deck the halls for the holidays, with parades, decorations, special activities. Our favorites include Universal Studios Orlando (loved our stay at the Loews Portofino), DisneyWorld (we had a really fun time at the Coco Key Hotel outside Disney, with its own waterpark and shuttle transport to the park), Busch Gardens Tampa (an outstanding zoo as much as it is a theme park) and Busch Gardens Williamsburg. Close to home and an absolutely delightful theme park destination is Hershey Park (particularly great for families with younger kids).

Dazzling holiday celebrations are in full swing at 10 Six Flags Entertainment Corporation parks. WinterFest at Kings Island, joined by Knott’s Merry Farm at Knott’s Berry Farm and Holiday in the Park at Six Flags Fiesta Texas were just named three of Top 10 Best Theme Park Holiday Events for 2025 by USA TODAY. Events are currently operating at Canada’s Wonderland: WinterFest; Knott’s Berry Farm: Knott’s Merry Farm; Six Flags Mexico: Christmas in the Park; Six Flags Fiesta Texas: Holiday in the Park; Six Flags Over Texas: Holiday in the Park; Six Flags Magic Mountain: Holiday in the Park; Kings Island: WinterFest; Carowinds: WinterFest; Six Flags Discovery Kingdom: NEW! WinterFest (a 2025 Best Theme Park Holiday Event nominee); Hurricane Harbor Oaxtepec: Christmas in the Park. Holiday escapes are available at Six Flags Great Escape Lodge (Lake George, NY): Holiday in the Lodge (thru Dec. 24; festive décor, themed activities, live entertainment and unlimited access to the indoor waterpark);Castaway Bay, Sandusky, OH (thru Dec. 31, meet and greets with Santa and admission to the indoor waterpark); Knott’s Hotel, Buena Park, CA, (thru Jan 4, 2026. holiday packages that include all-day drink wristbands, hotel parking, admission to Knott’s Merry Farm and a breakfast buffet option; and Schlitterbahn Waterpark & Resort, New Braunfels, TX. For event dates, links to tickets, visit www.sixflags.com or each park and resort’s website.

Make your own nostalgia. Happy holidays!

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