6. Old fashioned sleigh ride & ice skating in the White Mountains of New Hampshire

Sleigh ride at Nestlenook Farm in Jackson, New Hampshire

Nestlenook is the most picturesque area you could imagine for holiday festivities. The best thing to do here is take a classic wintry ride upon a horse drawn sleigh ride. Next, lace up your skates and head over to the ice rink on Emerald Lake for the most picturesque winter in the country setting. The gorgeous mountain scenery, chime music, and beautiful decor provides the perfect elegant setting for winter fun. When I imagine being in a Hallmark Christmas movie, this is the place I see!

Nestlenook Farm Ice Rink in Jackson, New Hampshire

7. Winter sleigh ride at the National Elk Refuge in Jackson, Wyoming

Photo opp at the National Elk Refuge

The National Elk Refuge provides habitat to 1000’s of elk at they come down from the mountains. We learned on our tour that as many as 6000-7000 elk migrate to the area for the food supply, beginning around October-November each year. 

Horse drawn sleigh rides (or a wagon in our case due to lack of snow) take you through the elk herd. We learned a lot of history and saw a lot of wildlife which was pretty exciting for city dwellers. The majestic snow capped mountains just add to the ambiance.

National Elk Refuge in Jackson, Wyoming

Taking this tour is the perfect treat after a hard day on the slopes and also a great alternative for non skiers to enjoy the scenery. Sleigh rides typically start running in mid-November and close up in March or April. You can read more about my experience visiting the refuge and see a lot more pictures of elk. We were told we didn’t see a lot of elk due to the warmer than normal temps, but I felt like we saw a ton. I couldn’t imagine how much you might see if you time your visit just right!

8. Skiing, ice skating, dining & shopping at Heavenly Village

Skiing in Lake Tahoe

Heavenly Village is a great dining and shopping village in Lake Tahoe. You can easily fill your day up with a range of festive activities including: ice skating, shopping, dining, movies, and of course, skiing! Skiers should be pleased as Heavenly is home to the area’s largest snowmaking system. An average annual snowfall topping 300 inches means plenty of opportunity for fun in the snow far into the New Year!

views of Lake Tahoe
Check out this stunning view from the observing area on the gondola ride!

Ski season typically runs from November-April. Visit the ski resort page for details regarding pricing, hours, and special events. After your day skiing or skating, there are many sporting goods stores, restaurants, and treat shops to enjoy. You will find everything from a Coldstone to a Patagonia.

9. Shopping along Chicago’s Magnificent Mile & State Street

Magnificent Mile in Chicago

Chicago’s Magnificent Mile shopping district is home to some of the best retail shops in the country. During the holiday season, all the trees lining N. Michigan Ave. are illuminated. I love browsing the shops and stopping for a cocoa or coffee when it’s cold out. It’s just a nice time to be in the city enjoying the festivities.

The shopping doesn’t stop at Michigan Avenue! Don’t forget about State Street, home to Macy’s famous holiday window displays. Growing up in Chicago, the highlight of the holiday season was our annual trip downtown to see the then Marshall Fields window and shop in the gorgeous 7 floor department store. While the windows are not nearly as festive now (this happened when Macy’s replaced Marshall Fields), I still visit anytime I am in the city for nostalgia sake.

Macy's on State Street Holiday windows in Chicago
One of the festive window displays – they change every season.

State Street is also home to numerous other shops and restaurants. Don’t miss out on the annual Magnificent Mile Lights Festival, which includes a festive parade, concerts by top artists, and a fireworks show over the Chicago River.

Update: I recently dined at the gorgeous Walnut Room, located inside the Macy’s on State Street. This beautiful long running restaurant (it opened in 1907) features a stunning 45 foot hanging tree as the centerpiece. I loved their wild mushroom ravioli and the Frango mint cheesecake. Reservations fill up fast, so I recommend booking right when they start allowing it (usually in late September).

The Great Tree at The Walnut Room on Macy's on State Street in Chicago
The beautiful tree decked on in a Marshall Fields theme for the 2025 season

**I hope you have enjoyed reading about some of my favorite getaways when the temps start turning frosty. Stay tuned for Part 2 as I continue my travel adventures!