labor day weekend getaway

Last Minute Labor Day Weekend Getaway Ideas (less than 3.5 hours from NYC)

Are you looking to getaway this Labor Day Weekend? Looking for last minute Labor Day weekend family vacation ideas from the New York Metro area? With Covid cases rising again, instead of flying, it’s safer to go on a road trip. Here are family friendly Labor Day Weekend vacation ideas that are less than 3.5 hours drive from the New York Metro Area.

5 Family Friendly Labor Day Weekend Getaway from the New York Metro Area

Families living in the New York Metro area are fortunate because there are so many vacation destinations within driving distance from New York. Whether you are looking for a family beach vacation or to relax at a mountain resort, it’s all an easy road trip from the New York Metro Area. All the family vacation ideas below are within 3.5 hours drive from the New York Metro area so they are ideal destinations for a Labor Day Weekend getaway. After all, you don’t want to spend most of your weekend driving! We have also included a lot of kid friendly, outdoor activities that everyone will enjoy during your Labor Day Weekend getaway.

1. Spend Labor Day Weekend in the Berkshires

The Berkshires is an easy Labor Day Weekend getaway destination for families in the New York Metro area. From Westchester County, the Berkshires is a quick 2 hour road trip- perfect for a quick Labor Day Weekend getaway. It’s also only a 3 hour drive from NYC. Aside from the easy drive, the Berkshires makes a great family vacation because there are a lot of kid friendly, outdoor activities.

canoe things to do with kids in berkshire

Kid Friendly Labor Day Weekend Activities in the Berkshires

Spending Labor Day Weekend in the Berkshires? Here are kid friendly, outdoor activities in the Berkshires.

  • Take the Kids Canoeing. You can take the kids canoeing this Labor Day Weekend. Book a guided canoe tour with Berkshire Canoe Tours. Admire the natural wildlife as you canoe down the tranquil Housatonic river. The guides at Berkshire Canoe Tours will take you and your family through a 2 hour canoe tour on the Housatonic river. Their canoe tours are suitable for both novice and experienced paddlers. Berkshire Canoe Tours starts at the Decker Boat Ramp at 298 New Lenox Road, Lenox, MA. Phone: 413-329-6017
  • Go Biking with the Kids. Take the kids biking in the Berkshires this Labor Day Weekend. Rent a bike and go biking with kids at Ashuwillticook Rail Trail. The 12 mile bike trail is kid friendly because it is a paved and level bike trail. You and your kids will enjoy biking along the picturesque Berkshire pond, Hoosic River, woods and farmlands. Pack a picnic lunch so you can stop for a break during your Berkshires family bike ride. Ashuwillticook Rail Trail parking and entry points are located at Lanesborough, MA and Adams, MA. Bike rentals are available from Berkshire Outfitters. Berkshire Outfitters is located 300 yards from Ashuwillticook Rail Trail at Rt. 8 Grove St., Adams, MA. Phone: (413) 743-5900
  • Go on a high speed Mountain Coaster with kids in the Berkshires! Take the kids to a Mountain Adventure Park in the Berkshires this Labor Day Weekend. Jiminy Peak Mountain Adventure Park is a great way to spend the afternoon with the family. Your kids will love riding the Mountain Coaster at Jiminy Peak. Imagine thousands of feet of twisting, turning fun through the woods! There are also other rides at Jiminy Peak’s Mountain Adventure Park such as Alpine Slide, Scenic chairlift rides, Giant Swing and a Euro Bungy Trampoline. There is also a rock climbing wall and a kids ropes course. If you are looking for fun outdoor activities with kids in the Berkshires, definitely plan an afternoon at Jiminy Peak Mountain Adventure Park. Jiminy Peak Aerial Adventure Park is located at 37 Corey Rd Hancock, MA. Phone: 413-738-5500

Family Friendly Hotels in the Berkshires

Jiminy Peak Mountain Resort

If you are looking for family friendly hotels in the Berkshires this Labor Day Weekend, then definitely consider staying at Jiminy Peak Mountain Resort. The units at Jiminy Peak Mountain Resort are condo-style accommodations with full kitchens right on the mountain. You can book 1 bedroom units or larger. It’s convenient to stay right at Jiminy Peak Mountain Resort because you have easy access to mountain biking, hiking, Jiminy Peak Aerial Adventure Park and Jiminy Peak Mountain Adventure Park.

Club Wyndham Bentley Brook

Club Wyndham Bentley Brook is another family friendly hotel in the Berkshires located at Jiminy Peak. Club Wyndham Bentley Brook hotel rooms are condo hotels with full kitchen. You can book a studio, 1 bedroom or 2 bedroom units at Club Wyndham Bentley Brook hotel. There are 2 pools at The Club Wyndham Bentley Brook, an indoor pool and a heated outdoor pool overlooking the slopes. There is also a large outdoor hot tub under a covered gazebo. Guests can also enjoy the Movie Theater, Arcade room and Arts and Crafts room at the Club Wyndham Bentley Brook. The hotel is very family friendly, it organizes family friendly activities for their guests such as Arts and Crafts, movie nights and family game nights/competitions. The Wyndham Bentley Brook is definitely a good choice for your Labor Day Weekend Getaway in the Berkshires.

Vacation Village Berkshires

Vacation Village Berkshires is another family friendly hotels for your Labor Day Weekend in the Berkshires. Located down the road from Jiminy Peak, Vacation Village Berkshires is a large resort family friendly resort in the Berkshires built on top of a hill facing Jiminy Peak. The units at Vacation Village Berkshires are condo-style units with a full kitchen. There are a lot of family friendly amenities at this Berkshire hotel such as indoor and outdoor pools, movie theater, basketball court, outdoor hot tub, playground, fire pit, barbeque grills and an indoor arcade room. Even though it is a big resort in the Berkshire, the units are located in small 3 story buildings so you are only sharing the floor with a few units and you don’t have to walk down a long hallway to get to your room. Similar to the Wyndham Bentley Brook, Vacation Village Berkshires has organized activities from family movie nights to arts and crafts activities for kids.

2. Take the Family to Vermont this Labor Day Weekend

Vermont is another easy Labor Day Weekend destination for families in the New York Metro area. Southern Vermont is an easy 3.5 hours drive from Westchester County.

Things to Do with Kids this Labor Day Weekend in Stratton

Stratton is the perfect Labor Day Weekend destination because there are many kid friendly, outdoor activities for the family.

  • Go on an ATV ride with the Kids. Take a guided ATV tour up Stratton Mountain. Your kids will enjoy the ride up from the base to the summit. Stratton Mountain Resort 5 Village Lodge Road, Stratton Mountain, VT. Phone: 802-379-1483
  • Go Paintballing with the Kids. Paintballing is a fun, outdoor activity for the entire family. You can book Paintball packages at Stratton Mountain Resort and they can equip you and your kids with everything you need to play Paintball. Stratton Mountain Resort 43 Sun Bowl Road, Stratton Mountain, VT
  • Go on a Scenic Gondola Ride. Take the gondola up to the top of southern Vermont’s highest mountain. Your kids will enjoy the gondola ride up to the peak at Stratton Mountain Resort. Enjoy spectacular views while you ride up in one of the Gondolas. From the summit, hike to the historic fire tower or explore one of the walking trails. Don’t forget to pack lunch so you can enjoy a picnic lunch with the family. Stratton Mountain Resort 5 Village Lodge Road, Stratton Mountain, VT. Phone: 802-379-1483

Family Friendly Hotels in Stratton

labor day weekend getaway stratton vt

Long Trail House at Stratton Mountain Resort

Stay at Stratton Mountain Resort for your family vacation this Labor Day Weekend. It’s centrally located to all the outdoor, family activities at Stratton Mountain. Long Trail House is a great choice for families because it is located across the street from Stratton Village and the hotel accommodations are condo-style. Each unit comes equipped with a fully stocked kitchen. And there is an outdoor pool for your family to enjoy. It’s also conveniently located across the street from Stratton Village so it’s an easy walk to the shops, restaurants and the gondolas.

3. Luxurious Family Beach Vacation in Rhode Island this Labor Day Weekend

Spend your Labor Day Weekend relaxing by the water in Rhode Island. A 3.5 hour drive from NYC, Rhode Island is a great family destination for Labor Day Weekend. Below you will find two family friendly resorts that you will want to spend your Labor Day Weekend in.

Family Friendly Resorts in Rhode Island

Weekapaug Inn

Looking for a luxurious, family beach vacation for Labor Day Weekend? You will love Weekapaug Inn. Weekapaug Inn is located on Rhode Island shoreline. Enjoy quintessentially New England accommodations that effortlessly combine casual comfort and luxury. It’s a family friendly resort that will pamper both you and your kids. You don’t have to lift a finger when you arrive at the hotel’s private beach, let the hotel attendants set up your beach umbrellas and beach chairs. Spend the day lounging on the beach while your kids are having fun crabbing and playing yard games with the hotel staff. Weekapaug Inn is the perfect Labor Day Weekend getaway destination for families in the New York Metro Area.

Ocean House

Take your family on a beach vacation this Labor Day Weekend. Spend the long weekend at Ocean House, a luxurious, seaside resort in Watch Hill, Rhode Island. You will love lounging on the hotel’s private white sand beach. Take a tour of the historic, New England resort. Celebrate the end of summer with a traditional New England lobster boil. Whatever you do, there are a lot of outdoor activities for families during Labor Day Weekend at Ocean House.

4. Family Beach Vacation in Connecticut this Labor Day Weekend

Looking for a closer beach destination this Labor Day Weekend? Connecticut beaches is only a 1.5 hour drive from Westchester County or a 2 hour drive from New York City making it an easy Labor Day weekend destination.

Connecticut Beachfront Resorts

Madison Beach Hotel Beachfront Connecticut
Photo Credit: Madison Beach Hotel

Madison Beach Hotel

Madison Beach Hotel is the perfect resort for your Labor Day Weekend getaway from the New York Metro Area. Just a 2 hour drive from NYC, you will love this beautiful resort on Connecticut’s coastline. Spend the day lounging at the hotel’s private beach. Or get a massage at the hotel’s full service spa. Grab a bite at one of the many restaurants at this quintessential Connecticut beachfront resort. If you are looking to spend your Labor Day weekend at the beach, Madison Beach Hotel is the perfect beach getaway!

water's edge resort and spa
Photo Credit: Water’s Edge Resort and Spa

Water’s Edge Resort and Spa

Another family friendly beachfront hotel for your Labor Day Weekend getaway is Water’s Edge Resort and Spa in Westbrook, CT. Take a swim in the outdoor pool. Spend the day lounging under your beach umbrella at the hotel’s sandy beach. Get a massage at the full service spa. Dine alfresco enjoying views of Long Island Sound at one of the hotel’s beachfront restaurants. You don’t even have to leave your Connecticut beachfront hotel to enjoy your Labor Day weekend beach getaway!

5. Labor Day Weekend in Mystic, CT

Mystic is an easy Labor Day weekend getaway destination from New York City and the surrounding New York metro area. It’s a quick 2 hour drive from Westchester County and only a 2 hour and 30 minutes drive from NYC. From visiting Beluga whales to exploring the quaint New England seaside town, there are a lot of kid friendly, outdoor activities in Mystic.

kid friendly mystic ct

Family Friendly Labor Day Weekend in Mystic, CT

Mystic is a great Labor Day Weekend getaway for families. Below you will find things to do with kids during your Mystic Labor Day Weekend getaway.

  • Visit the Beluga Whales at Mystic Aquarium.  Take the kids to Mystic Aquarium this Labor Day Weekend. Unlike the typical aquarium where most exhibits are housed indoors in one building, Mystic Aquarium is more similar to a zoo where many exhibits are located outdoors. Kids will enjoy seeing the penguins, beluga whales and seals! Mystic Aquarium at 55 Coogan Blvd, Mystic, CT
  • Watch the Mystic Drawbridge in Action. While exploring downtown Mystic this Labor Day Weekend, take the kids to watch the Mystic Drawbridge in action! The best spot to watch the Mystic Drawbridge are from the outdoor seats of the Mystic Drawbridge Ice Cream Shop. The Mystic Drawbridge Ice Cream Shop is located right next to the Mystic river on Main Street. It’s a great spot to enjoy your ice cream while taking in the views of Main Street, Mystic River and the Mystic drawbridge. Even if you don’t see the drawbridge in action, your kids will still enjoy watching the boats go by the Mystic River and the hustle and bustle of this New England seaside town. Mystic Drawbridge Ice Cream at 2 West Main Street, Mystic, CT.
  • Take the Kids Kayaking. If you are looking for something active to do with kids this Labor Day Weekend, kayaking or paddle boarding is a fun activity in Mystic. You can rent a kayak or paddle board from Adventure Mystic. Adventure Mystic is located right on Mystic River. Rent kayaks and paddle boards by the hour or by the day. Single Kayak rentals start at $25 per hour and Tandem Kayak rentals start at $40 per house. Your kids will enjoy kayaking down Mystic River during your Labor Day Weekend getaway in Mystic, CT. Adventure Mystic is at 15 Holmes Street, Mystic, CT.
New York Weekend Getaway to Mystic, CT

Kid Friendly Hotels in Mystic, CT

Hilton Mystic

If you plan to visit Mystic Aquarium, the Hilton Mystic is ideally located for your Labor Day Weekend getaway. It is conveniently located across the street from Mystic Aquarium and the Olde Mistick Village. It is also across the street from many kid friendly restaurants and only a 6 minute drive to downtown Mystic. Plus the Hilton Mystic was recently renovated so it is nice to come back to a newly renovated room.

Inn at Mystic

The Inn at Mystic is another kid friendly hotel for your Labor Day Weekend Getaway in Mystic, CT. It is located overlooking the Mystic Harbor. There are a lot of kid friendly amenities onsite including an outdoor pool, tennis courts, basketball court, walking trail and kayaking. Plus the rooms at The Inn at Mystic were recently renovated.

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