5 Weekend Trips Outside of the City With Your Littles (don't forget your Remi Playard!)

Ready to escape the city with your crew? We've picked five cool spots to try with your little one (and your UPPAbaby Remi) in tow. Choose your speed: Relax, Adventure, Learn, or all of the above!

For The Lover of all things Luxe:

Where to go: Peapack, NJ

Where to stay: Pendry Natirar

Driving Time: 1 hour

Itching for a luxury getaway that's close, easy, and ultra chic? Look no further than the lush green center of the Garden State. This weekend destination is purely about R&R. Pendry Natirar is gobsmackingly gorgeous: The large Tudor-style manor house looks like it was plucked out of the Cotswolds, set amidst lush farmlands and 400 acres of rolling hills. Activities at the property are plentiful, from hiking, tennis, archery, and biking to picking herbs, birding, or soaking at the spa. If you want to go at it alone during the day, the kiddos can play at Paintbox, Pendry's signature children's club with all-day activities (think farm tours, group games, locally inspired arts & crafts, or outdoor eco-adventures) for children 5-12 years old. If you little one is a bit bittyer, take them with to explore the vast property. There are even UPPAbaby strollers on hand if that's how you like to roll (and who doesn't!). 

image courtesy of Pendry Natirar

For The Skier & Nature Enthusiast: 

Image courtesy of Eastwind Hotel

Where to go: Windham, NY

Where to stay: Eastwind Hotel

Driving Time: Approximately 3 hours and 20 minutes from NYC

This stylish and welcoming retreat in Windham, NY (ski territory!) is the perfect spot for a weekend out of the city, where you can slow down and take in the nature all around you, or if you're so inclined, hit the slopes. [If you do, and have a 3rd, 4th, or 5th grader, purchase a SKI NY Free for Kids Passport.]

As for where you should stay for your weekend adventure:  Eastwind Windham was just refurbished in winter 2025, and makes a perfect family retreat. In fact, they've recently unveiled a brand new Mountain House overlooking Windham Mountain as well as 32 Scandi-chic additional guestrooms. If you're bringing a baby or toddler, cribs are provided upon request. 

When it's time for dinner, you can enjoy a family-style feast at the BunkHouse Lounge, and then follow it up by the firepit with s'mores kits to enjoy a sweet evening under the stars. After skiing, hiking, or snowshoeing by day, relax in one of the two wood barrel saunas. If the sun's out and the temperature suits, read a book and relax in one of the hammocks in the meadow. 

Enjoy your time at Eastwind Windham? There are other locations of the Eastwind properties, both in Oliverea Valley and Lake Placid to check out as well! 

For The Outdoor Activity Enthusiast: 

Image courtesy of Mohonk Mountain House

Where to go: New Paltz, NY 

Where to stay: Mohonk Mountain House

Driving Time: Approximately 2 hours, 40 minutes from NYC

The Mohonk Mountain House, a Victorian castle resort nestled in Hudson Valley, has long been a storied escape from the city for families. Not surprising, as the property itself has been family owned by the Smiley family since 1869.

The plum property sits on a majestic lake and is surrounded by 40,000 acres of forest. making it a ripe spot for a wide range of activities from swimming, paddleboarding or fishing in the lake, to hiking, archery and more.

For your little ones, there's a wonderful Kids Club (for ages 4-12) where your children can enjoy activities like art projects, inflatable obstacle courses, or nature walks. After a long day, settle in by the campfire for some well-earned s'mores.

If you want to sneak out to the spa for a couple's massage as baby takes their afternoon nap, no problem, there are babysitters that can be arranged for a fee. 

Image courtesy of Mohonk Mountain House

Posted rates are all-inclusive, so you don't have to think about meals as an extra. It's easy to nab a highchair at the restaurant, and there are cribs and other baby-friendly amenities upon request for your room.

Image courtesy of Mohonk Mountain House

For The History Buff:

Where to go: Mystic, Connecticut 

Where to stay: The Whaler's Inn

Driving Time: Approximately 3 hours and 30 minutes from NYC

Head up north to beautiful Mystic, Connecticut, home of the famous Mystic Aquarium, Mystic Seaport Museum, and of course Mystic Pizza for a back-in-the-day movie reference. At the Mystic Aquarium look forward to spying beluga whales, jellyfish, penguins, clownfish and even a live seal presentation. 

The Seaport Museum is interactive with a fully recreated historic village which is totally hands-on, and your family can even tour one of the country's last surviving whaling ships, the Charles W. Morgan. 

If you hold off until March 28 or thereafter, you can see the Brickwrecks: Sunken Ships in Lego® Bricks exhibit.  And, if it's warm enough and your kiddos are craving an outdoor adventure, head to Tree Trails Adventures, for an afternoon of climbing and ziplining. 

As for accommodations, we suggest that you book a Junior Suite at the Whalers Inn, a premier boutique property in Downtown Mystic. A site of hospitality for over 125 years, The Whaler's Inn is comprised of six buildings from different historical eras, each with a rich and unique history.

The folks at The Whaler's Inn have been super intentional about making it a comfy spot for families. Case in point: Several of the Junior Suites have built in bunk beds with individual reading lights, a custom neon anchor sign, and even a children's library filed with thoughtfully curated picture books.

On top of all this, every afternoon, the Inn delivers freshly baked cookies, a sweet pick-me-up before heading off for your next adventure. 

For The Cottegecore Champ (#dollhouselife):

Image by Kate S Jordan

Where to go:  Hudson Valley 

Where to stay: Six Bells Inn, Rosendale, NY

Driving Time: Approximately 2 hours and 40 minutes from NYC

Although there are lots of choices of quaint spots in Hudson Valley, we were drawn to the new The Six Bells Inn, which looks as if it were plucked right out of a storybook. 

The inn, which opened in 2025, brings the spirit of the countryside to the region. Inside the historic three-story building are eleven vintage-chic guest rooms each with their own character. Also on sight: a tavern, riverside restaurant, and shop. Don't miss the adorable little library for bookish kiddos winding down from a fun day of exploration.

So what is there to do in the area?  If you're up for adventure: Hike Dover Stone Church, Overloop Trail at Overlook Mountain, or check out the Harness Racing Museum and Hall of Fame. You're also close to both Kingston (Check out the Hudson River Maritime Museum and lunch at Hotel Kingsley) and Woodstock (explore Tinker Street, Woodstock Waterfall Park or catch a play at the Woodstock Playhouse), two spots with super cute downtowns to explore. Also, if you visit in the summer, theres nothing more magical than the Hudson Valley Hot Air Ballon Festival that takes place mid-July. If you want to keep things lower key and just check out your surrounds, the town of Rosendale itself features quirky stores, vegetarian-friendly eateries, and even a once-a-year pickle festival that takes place in the fall.

Image by Tory Williams