
Unlocking the Wonder
Navigating Toddler Travel with Ease
By Faith Dwight
Updated August 14, 2025
Our Do-able in a Day series highlights road trips from bigger cities. So whether you’re local to one of these destinations, or taking a trip to the city but eager to venture out for some family fun, you’ll find adventures under a two-hour drive that are perfect for day trips, overnights, or weekend getaways.
Whether you live in Manhattan and need a quiet weekend outside the city, or are just visiting the Big Apple and want to explore the surrounding area, there’s an abundance of fun and beauty to be found within just a couple of hours by car or train.
Distance from Manhattan: 2 hours 40 minutes (A little more than our normal two-hour cut-off, but we think it’s worth it.)
Accessible by train? Yes
Why it’s worth it: Rent bikes for the whole family (including toddler seats) and explore the area’s endless bike trails. Get in touch with nature and feed the ducks at the Duck Pond in East Hampton. Spend a long day on the beach followed by a belly full of pizza from Brooklyn favorite Roberta’s Montauk location. For a treat, don’t miss frozen yogurt at Buddhaberry in Sag Harbor or an old-fashioned root beer float at Southampton’s Sip’n Soda.
Where to stay: Gurney’s Resort, Montauk Yacht Club, and Breakers (all in Montauk)
Distance from Manhattan: 1 hour 40 minutes
Accessible by train? Yes
Why it’s worth it: Less than two hours away from Manhattan, North Fork feels like a different world. Best visited in summer, North Fork’s largest town, Greenport, may be right up your street if your family vibe is a little more laid-back than Montauk or the Hamptons. Spend long days on the beach followed by slow evenings at family-friendly Crabby Jerry’s. Take a ride on the antique carousel at Mitchell Park, or sip wine and listen to live music at one of the local wineries, while kids run free through grapevines.
Where to stay: A beach bungalow at Silver Sands Motel in Greenport
Distance from Manhattan: About 1 ½ hours
Accessible by train? Yes
Why it’s worth it: In New Paltz, where you stay is part of why you should go in the first place. Mohonk Mountain House is a Victorian castle resort surrounded by 40,000 acres, with loads of family-friendly activities included in your overnight rate. Take advantage of hiking, boating, swimming, archery, skiing - even a Kids’ Club! - at no added cost. Meals are also included, which makes the whole stay incredibly low-stress. New Paltz itself is a quaint college town also worth exploring…if you can drag yourself away from Mohonk!
Where to stay: Mohonk Mountain House, an iconic Victorian resort
Distance from Manhattan: 2 hours
Accessible by train? Yes
Why it’s worth it: Grab coffee at Moto Coffee/Machine and head to Henry Hudson Waterfront Park to watch the boats go by. When little legs are worn out, head back to our fave place to stay: Hudson hotel Rivertown Lodge. A destination in itself, it’s a former movie theater-turned-inn conceived by New York design firm Workstead and built by local craftsmen. The lodge boasts comfy lounges flanked by wood stoves for chilly evenings, 24-hour pantries for cases of the late-night munchies, bikes to borrow, and a relaxing backyard with picnic and ping-pong tables. (It’s also one mile away from the Hudson Amtrak station.)
Where to stay: Rivertown Lodge
Distance from Manhattan: Just under 2 hours
Accessible by train? No
Why it’s worth it: Step back in time in one of the area’s quaint historic towns, like Honesdale (where your tiny train-lovers can explore a full-size replica of the first locomotive to run on commercial track in the USA at the Main Museum) and Stroudsburg. If you’re into outdoor adventures, we recommend the area around Dingmans Ferry, where easy access to hikes lead to the area’s many picturesque waterfalls - perfect for a splash on a hot summer day.
Where to stay: Kalahari Resort in Tobyhanna, if you’re into water parks. Skytop Lodge if you’re not.
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