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Family Fun in 5 Hudson Valley Towns

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The Hudson Valley was my family’s summer playground when I was a kid. Close enough to New York that the kids could handle the drive; far enough that you feel you are away; with plenty of nature, cute small towns, and historic sites to make the vacation well-rounded.

The Hudson Valley is still an ideal destination for day trips or weekend jaunts from several parts of the Northeast, but especially New York City. You’ll find year round attractions as well as distinct activities in each of the seasons. Ski in winter, swim and hike in the warm weather, and leaf-peep in the autumn.

Below, Vanessa Ahern, a Hudson Valley resident, gives us the scoop on her favorite places to visit with her 7 and 10-year-old daughters.

Here are her top 5:

Mt. Tremper/Phoenicia

this Hudson Valley train ride is a holiday season treatMy husband and I fell in love with this area before we had our kids, but they’ve helped us find the family friendly side of this off-beat destination. First, there is the Catskill Mountain Rail Road  ride along the Esopus River. We enjoy the scenery while the kids like bumping along on the old fashioned train.

Holiday Bonus: In November and December, Santa Claus is on board for select train rides.

After the train, stop by the hard-to-miss Emerson Resort, whose collection of shops includes the Kaleidostore, an astronomy-themed toy store that houses the world’s largest kailedoscope . Enjoy the 8-minute Kailedoscope show then afterward take a break at the shoping complex’s café.

Begin or end your day in Phoenicia, officially one of the coolest small towns in the U.S. In the morning try the enormous pancakes at Sweet Sue’s. Or head to Brio’s Pizzeria at lunchtime for wood-fired-oven pies. Of course, there’s the Ice Cream Station for an afternoon treat.


rhineback is a quaint hudson valley townReward your kids after a long car ride with a romp through the beautiful playground at Lions Mini Park within walking distance of the town center. It also has a small pond, ducks, picnic tables and a fenced-in area for toddlers. There’s a popular year-round farmer’s market on Sundays from 10:00 am to 2:00 pm, great for sampling local seasonal produce and other goodies. And we love the pancakes at Pete’s Place. The Dutchess County Fairgrounds  is host to dozens of festivals throughout the year.

Family favorites include the County Fair in later summer, the antique auto show in spring, and the Sheep and Wool Festival in the fall.

Holiday Bonus: My favorite even in Rhinebeck is the Sinterklaas Festival in early December. Enjoy a puppet show, children’s parade, dance performances, free holiday treats, arts & crafts and a generally festive atmosphere.


small chocolate dogs from Lucky Chocolates in the Hudson ValleyAt Any time of year, head to Lucky Chocolates in town to warm up. Kids and adults will go ga-ga over the spread of artisinal organic and fair trade chocolates.

The place to start a cool-weather visit is Kiwanis Ice Arena, an Olympic-size skating rink. It’s located in in Cantine Field, which also has a a small wading pool for the tots, tennis courts and ball fields for warm-weather visitors.

In warm weather, explore the Opus 40 sculpture garden or visit the Catskill Animal Sanctuary.


The town’s Trevor Zoo is a hidden gem where you won’t have to fight crowds here to see plenty of exotic animals. If the kids still have energy when you’re done, head to Tribute Garden Park in town for its pirate ship, fire truck, and spiral slide.

Pine Grove Ranch and Rocking Horse Ranch

If you’re staying the weekend and want to make sure to tire the kids out for an early bedtime, book a night stay at the Rocking Horse or Pine Grove resorts. Both offer horseback riding, indoor and outdoor pools and waterplay areas, supervised kids activities, entertainment and tons of things to do. Send older kids zip lining while you head to spa. Then meet up for dinner. Rocking Horse has onsite dining while Pine Grove visitors will find good family-friendly variety in nearby New Paltz.

Vanessa Ahern blogs about Hudson Valley food, events and destinations at Hudson Valley Good Stuff.

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