Appealing Upstate New York Towns to Celebrate the Holidays

Catskill Mountains | Image credit: Clay Banks

If you are looking for a scenic place to enjoy the holidays, you will have plenty of excellent options across Upstate New York. With lively atmospheres, family-friendly offerings, and a picturesque location, Upstate New York communities are ideal winter destinations to visit. Let’s look at two appealing towns here that are perfect for a holiday retreat.

Kingston

Kingston is a historic community, originally settled by the Dutch in the mid-17th century and was New York’s first capital city. Today it is a picturesque little town, home to around 24,000, located along the Hudson River. Kingston is famed for its historic architecture, thriving arts community, and busy downtown that hosts numerous unique shops and restaurants. Its quaint atmosphere is only improved come the holidays. 

Many family-friendly events can be enjoyed in Kingston throughout the holiday season. The old-fashioned Catskill Mountain Railroad, a big part of the town’s tourism, takes visitors across scenic sites in the Catskills. Over the holidays, the Catskill Christmas Express involves Christmas decor, visits from Santa, and hot chocolate served by Santa’s elves.

Heavy snowfall and gorgeous architecture make for a dramatic holiday setting in Kingston’s downtown, which is adorned with holiday lights to add to the festive look. Outside Kingston you can visit A Frosty Fest—a large holiday festival with a light show, Christmas characters, gift shops, and holiday foods. Kingston has an abundance of exciting options that will give families a holiday to remember.

Catskill Mountain Railroad | Image source: Catskill Mountain Railroad Co. (Facebook Page)

Troy

Troy is a gorgeous little city on the east shore of the Hudson River and a short drive from Albany. It is another historic city with a claim to fame as the birthplace of the iconic Uncle Sam image, and it is also known for its vibrant downtown and gourmet food scene. Troy is a city that pulls out all the stops for the holidays, making it a must-see for anyone looking to enjoy a seasonal getaway in Upstate New York.

The most famous element of Troy’s seasonal celebration is the downtown Troy Victorian Stroll. This year will be the 40th version of this holiday tradition, which features people dressed in classic Victorian attire, live holiday music, arts and crafts, seasonal treats, and other fun family-friendly activities.

Troy’s picturesque downtown is transformed into a winter wonderland with holiday lights and decorations. This year will be the inaugural Troy Glow festival, a public art light festival downtown, where many of the shops and restaurants in the city will have colorful light installations. The downtown is also an excellent place to take care of your holiday shopping, with many stores offering local handmade artisanal goods.

Troy Victorian Stroll | Image source: Saratoga Living (Facebook Page)