There’s nothing better than NYC in the summertime — tons to do and a little more breathing room for everyone. Still, sometimes you want to be the one to get out of town. Shelter Island and Montauk are great spots for a weekend getaway with the family. Want to take the brood on an adventure through the wilderness? Craving some time by the shore? These two beach towns offer plenty of fun for everyone. Here’s the scoop on where to go and what to do while you’re there.

photo: Michelle Cohen

Shelter Island
This beach haven is a 2.5-hour drive from Manhattan, plus a short ferry ride. It’s nestled between the North and South Forks of Long Island. Pristine beaches, casual restaurants and water sports are just some of what it has to offer. Get ready to experience the perfect mix of relaxation and exploration.

photo: Christie O. via Yelp

How to keep ’em busy
Lather on your sunblock and grab a backpack. A weekend on Shelter Island means lots of time outdoors. Mashomack Preserve is one of the island’s top attractions. It features 12 miles of coastline and there is enough wildlife to keep little nature lovers entertained for hours. The preserve is also home to over 200 species of birds. You’ll spot beautiful scarlet tanagers and Baltimore orioles in the tree canopies and red-tailed hawks in the open meadows.

If hiking isn’t your thing, opt to tour the area by kayak. Shelter Island Kayak Tours offers a two-hour trip around Coecles Harbor that includes great views of Mashomack. Water and snacks are provided in case the kids get hungry.

photo: via Shelter Island Whales Tale Facebook page

For a more laid back activity, challenge the family to 18 holes at Whales Tale Mini Golf. Then head over to the cafe, which serves freshly-stuffed homemade cannolis. Or, spend the evening at the Shelter Island Tennis Club, where they host a Pee Wee program for kids ages four to seven from 5 p.m. to 6 p.m. everyday. While your little Federer is practicing his strokes, you can join the club’s Sunset tennis clinic and get in some match play.

If you’re planning on spending a full week on the island, Sylvester Manor offers a week-long camp for kids. The Young Farmers Program gives campers ages five to eight a chance to learn about sustainability, local food, farming and nutrition. Younger kids ages three and four can take part in the Manor’s Imaginarium camp, which features farm-themed games, arts and crafts and gardening.

photo: Michelle Cohen

Where to take a dip
Wades Beach and Crescent Beach are best for families. Both have life guards and roped off areas. Crescent, located on the north side of the island facing Southold and Greenport, is one of the most popular beaches in town. It is the only beach on the island with restaurants, so you can lunch while you’re there. Wades, on the south side of town, has a shallow area for young swimmers and restrooms nearby. Menhaden Lane Beach and Shell Beach are two other spots known for their excellent views. Parking at any beach on Shelter Island requires a permit; a daily beach parking pass is available at the Town Clerk’s office at Town Hall. Weekly passes are available for $35.

photo: via The Rams Head Inn Facebook page

Where to grab a bite
Good news: Most restaurants on Shelter Island are family-friendly. The Pridwin Hotel hosts a Wednesday night cookout with live music from July 1 through Labor Day that everyone in the family will enjoy. The menu is all-you-can-eat with options like fried flounder, chicken fingers and hamburgers.

Stars Cafe offers some of the best pastries on the island. It’s croissants, muffins and scones are made from scratch and freshly baked every morning. For brunch, take a trip to The Shelter Island House, where the little ones will enjoy traditional breakfast foods like french toast or scrambled eggs with home fries. Salt Waterfront Bar and Grill is another good option. The gastropub provides fantastic views and specializes in fresh and local foods; we recommend like the grilled shrimp bruschetta, fish and chips or local littleneck clams.

Have a sitter? Be sure to plan a date night. The Rams Head Inn is a romantic option with a seasonally focused farm-to-table menu. Request the back lawn when booking your reservation for views of the harbor. If you’d like to go somewhere more trendy, Sunset Beach Restaurant is a hip spot with great food, cocktails and nightlife.

photo: Michelle Cohen

Family-friendly lodging
With its selection of cottages, The Pridwin is one of the most kid-friendly spots on the island. Accommodations include a complimentary breakfast plus access to the hotel’s private pool and beach. Water lovers can rent kayaks, sunfish or paddle boats to use on the bay, and bikes are available for exploring the island.

The pricey Chequit Inn is worth the money if you want to splurge. All of the rooms are recently renovated, comfortable and elegant. Dering Harbor Inn is another great spot, with waterfront villas for families and a location that’s a five minute walk to the main village. Children under 10 stay for free and cribs are available at no extra charge. Young guests can enjoy the heated pool and tennis courts and roam the inn’s seven acre grounds.

photo: Hector M via Yelp

There’s a reason New Yorkers make the four hour drive to the far eastern tip of Long Island every weekend. It’s remote and laid back, yet offers plenty to do for families looking to get out and about. The destination also offers some of the most beautiful beaches in the area. Take a trip out there and see for yourself!

How to keep ’em busy
Montauk is a hiker’s paradise. Shadmoor State Park features trails across 99 acres. It’s a great spot for new parents who are looking for some outdoor fun while the little one naps in the Ergo. Older kids with a little hiking experience will enjoy the trails as well. Some of the park’s highlights include freshwater wetlands, bluffs and elevated platforms that are ideal for birdwatching. If you only have time for a quick hike, head to The Walking Dunes at Hither Hills State Park; this 3/4 mile trail features views of dune areas reaching 80 feet tall.

Don’t leave town without going for a tour of the Montauk Light House. Children over 41 inches can climb the 137 steps up to the top tower; kids who don’t meet the height requirement can learn about the history of the lighthouse in the museum and run around the grounds.

If you want to treat your kids to a new experience, sign them up for riding lessons at Deep Hollow Ranch. The establishment holds a Summer Pony Camp for riders ages seven to 12, and also offers wagon tours around the premises and surrounding areas. Rita’s Stable Petting Zoo is a good spot to take toddlers; your little animal lover will meet sheep, rabbits, chickens, geese, peacocks, donkeys and more.

No family trip is complete without a little putt putt. PuffnPutt is a minigolf course featuring 18 holes that range from easy to challenging. Added bonus: If you score a hole in one on the 18th hole, you’ll win a free game.

photo: L C. via Yelp

Where to take a dip
There are so many family-friendly beaches in Montauk you really can’t go wrong. If you’re staying in town, Gin Beach and South Lake Drive are two of the closest beaches with lifeguards and calm shallow waters for kids. Abraham’s Landing and Maidstone Park in Amagansett are two other options to mix things up during your stay. You might also like spending the day at the state park beach at Hither Hills, where lifeguards are on duty and there’s playground behind the dunes.  

photo: Joi S. via Yelp

Where to grab a bite
If you want to fill up on local seafood, Montauk is home to plenty of establishments eager to indulge you. South Edison is just south of town and has one of the most interesting dinner menus in Montauk. Order the olive oil braised baby octopus tacos and chili dusted local sea scallops for yourself; the kids will enjoy the rock shrimp and devour the ice cream sandwich bites for dessert.

For lunch, enjoy some lobster rolls while sitting on the outdoor picnic tables at St. Peter’s Catch. This casual lunch spot doubles as a fish market so everything on the menu is fresh. If you’d like a light and healthy meal, Naturally Good Food & Cafe features a comprehensive breakfast and lunch menu. We recommend the shop’s signature sandwich, The Bruce, which is made with fresh caught local yellow-fin tuna.

photo: Julie M. via Yelp

If you end up missing the tastes of home, you can also give your favorite NYC establishments a try out east — both Zum Schneider and Red Hook Lobster Pound both have outposts in Montauk and are safe bets if you want a good meal. (Take note: devoted fans say Red Hook Lobster Pound serves the best lobster rolls in Montauk.)

Family-friendly lodging
If you’re into luxury camping, plan to stay at Ruschmeyer’s. The spot features cabin-inspired guest rooms and a central lawn with picnic tables, grills and hammocks. Kids will enjoy taking part in the special lawn games and bubble activities and adults can choose from bicycling, ping pong, yoga and taking a paddleboard for a spin.

photo: Ruschmeyer’s via Yelp

Gurney’s Montauk is a popular resort known for its Seawater Spa, where kids can take a dip in a heated seawater pool and you can get a massage. One thing to keep in mind: the resort is in the process of updating its accommodations, so be sure to request a renovated room when you book a reservation.

If you’re on a budget, The Ocean Resort Inn is a charming and offers great value. The rooms are clean and many have scenic ocean views and a central courtyard offers porch swings, hammocks and barbecues for chilling out. Bonus: the Inn’s new heated saltwater pool is making its debut this summer.

Do you have a favorite summer getaway spot? Tell us about it in the comments below!

–Michelle McIvor Cohen


Your daily dose of joy and connection
Get the Tinybeans app