The pool at Baron's Cove beckons even at sunset.

Not Your Typical Hamptons Town

Sag Harbor, New York
If you think the Hamptons are pretentious and exclusive, Sag Harbor leans toward low-key and inclusive. In spite of its well-heeled residents, it manages to maintain traces of its authentic maritime history. Hopefully the sun will shine during your stay, because Sag Harbor’s bay beaches feature gentle waves that are just right for your toddler's first swim. This former whaling port is home to the Sag Harbor Whaling Museum, an excellent rainy day activity. Charming Main Street is loaded with shops and eateries. The Sag Harbor Variety Store is a classic five-and-dime. Kids will delight in the old-fashioned mechanical pony ride, art supplies and retro toys. 

Stay: The can-do staff at the recently renovated Baron’s Cove will make you feel welcome from the moment you arrive. The comfortably elegant vibe at this 67-room waterfront hotel is as relaxed and breezy as a late summer afternoon. 

The guest rooms are bright and airy, decorated in a clean, nautical style. The center of activity is the sun-drenched pool with a view of the marina where the yacht-club set meets the preschool set. In the late afternoon, live acoustic music enhances the scene. Complimentary beach passes, hula hoop classes, a tennis court, ping pong, bean-bag toss and bikes are just a few of the property’s perks. The restaurant serves an irresistible menu of traditional New England fare with dishes that will tempt the most finicky kid’s appetite. This beach-chic hotel is pet-friendly, so bring the pooch. 

Getting there: Sag Harbor is a two hour drive from NYC, but of course we all know that it can take much longer in traffic, especially a holiday weekend like Labor Day. Ride the Jitney and make it a car-free getaway. Baron’s Cove is walking distance from all attractions and provides a complimentary shuttle to the beach. 

RELATED: Hamptons and North Fork Guide for Families

Wild Ponies in Virginia

Chincoteague, Virginia
Enjoy a Southern Labor Day retreat with a trip to Chincoteague or next-door neighbor Assateague Island, located respectively on Virginia and Maryland’s Eastern Shores. Famed for wild ponies, this area’s reputation blossomed with the publishing of the children’s literary classic, Misty of Chincoteague. You’ll find plenty of hotels and restaurants in Chincoteague and unspoiled beaches in Assateague. 
The flat Island Nature Trail is perfect for strolling and cycling. Take a family-friendly boat ride, kayak or just enjoy Mother Nature at her coastal finest. The annual Pony Swim takes place in July, but you can catch a distant glimpse of these beautiful animals from one of the pony viewing areas anytime of year. 

Stay: Chincoteague’s peaceful Refuge Inn is within walking distance of the wildlife refuge. They have ponies living on site, so the kids will have a ball watching them play. 

Getting there: It’s a five hour drive from NYC.

More Than Baseball in Upstate New York 

Cooperstown, New York
The Baseball Hall of Fame is Cooperstown’s big draw, but there’s an abundance of family-friendly offerings in this New York town even if you don’t give a hoot about America’s favorite pastime. The Farmers’ Museum, Fenimore Art Museum, the acclaimed Glimmerglass Festival and serene Lake Otsego are a few of its many gems. The village exudes a Mayberry vibe, so expect old-fashioned ice cream parlors and a cool lake breeze to announce the end of summer. Swimming, canoeing and other paddling adventures can be had in several Cooperstown spots, as well as hiking.

Stay: The commanding Otesaga Hotel sits directly on the lake. Rocking chairs on the porch, old-world service and one of the best breakfast buffets in the Northeast make it special. 

Getting there: It’s a four hour drive from NYC.

The outdoors, outlet shopping and seafood aplenty in Maine.

Shopper’s Paradise on Maine’s Coast

Freeport, Maine
Active families will flip for Freeport, Maine. You can learn a new sport or perfect an old one for only $25 at the L.L. Bean Outdoor Discovery Schools. Always wanted to try stand-up paddle boarding or kayaking? Archery or fly-fishing on your bucket list? This Maine retailer provides all equipment and top-notch instruction. Kids ages six and older are welcome to most classes, so it’s a great family activity.

This retail-rich town is a tween shopper’s dream. It is famous for being the home of the L. L. Bean flagship store, open 24/7, but there are dozens of name-brand outlets clustered in the pedestrian-friendly downtown. Day trip it to stunning Popham State Beach Park and let the kids play in the tide pools while you enjoy a lobster roll from nearby Percy's Store.

Stay: The Harraseeket Inn has 93 rooms, a large indoor pool and a great location in the heart of town. Book directly through the hotel’s website and they throw in breakfast and afternoon tea.
If you like the friendly feel of a B & B, the White Cedar Inn welcomes children in several of its rooms. Rooms are very clean and the innkeepers cook up a hearty breakfast each morning. 

Getting there: Freeport is a five-to-six-hour drive from NYC. Fly to Portland in an hour, rent a car, drive 20-30 minutes north and you’ll be there in a jiffy. Take some time to explore Portland’s dynamic food scene for dinner before piling back into the car.

History in the Hudson Valley

Hyde Park, New York 
Hyde Park is a great choice for those families with older children. Franklin and Eleanor Roosevelt called this town home and exploring the area may spark thoughtful conversations about the American presidency. There are innovative programs at several historical sites that cater to kids. At the F.D.R. Presidential Library and Museum, costumed interpreters add a theatrical flair. At Val-Kill, Eleanor Roosevelt’s home, teatime chats called “Cottage Conversations” encourage curious kids to ask questions about Eleanor while sipping tea and nibbling cookies. Catch a film at the Hyde Park Drive-In Movie Theater, visit the interactive Mid-Hudson Children’s Museum in Poughkeepsie or head to one of the valley’s pick-your-own farms. 

Stay: The functional Courtyard by Marriott in Poughkeepsie won’t win any awards for quaint, but it’s clean, comfortable and has an indoor pool. If you’re seeking charm, head a few miles north to the Beekman Arms, built in 1766. 

Getting there: Hyde Park is about a 100-minute drive from Manhattan.

RELATED: Thomas Land Theme Park Opens in Massachusetts

Parent Pamper Session at Relaxing Spa 

Plymouth, Massachusetts
Sometimes you need a little R& R without the kids. The Mirbeau Inn & Spa in Plymouth, Massachusetts offers adults the ultimate in pampering. It looks like a French chateau, surrounded by gardens with a soothing waterfall and Koi ponds. The 50 rooms and spa are fit for royalty. Treatments are tempting, but all hotel guests have unlimited access to the spa and fitness center, so there’s no pressure to book a spa service. The farm-to-table onsite dining options are delicious.

If you can pull yourself away from the hotel's gorgeous confines, historic Plymouth is home to Plymouth Rock, a replica of the Mayflower, Plimoth Plantation and numerous other venues that pay homage to the Pilgrims. Feel the sand between your toes at Duxbury Beach Park for the ultimate last taste of summer. 

Getting there: Mirbeau is a four hour drive from NYC.

Car-challenged? We get it. Try one of these car-free Labor Day Weekend suggestions, or check out our Events Calendar for great staycation activities like testing out the new Battery Park carousel or camping right here in NYC.