Cute Towns on Long Island With Walkable Main Streets
Compared with the walkable nature of New York City, suburban life can sometimes make you feel tethered to the car. But on Long Island, that doesn't have to be the case. The region is filled with cute towns, home to walkable main streets, great for parade watching, farmers market shopping, or perusing a pop-up craft fair.
Whether you're new in town or you're a longtime local, we've found 13 cute towns whose main drags feature plenty of family-friendly fun, from local museums to historic sites and beachfront parks, family-friendly restaurants, irresistible ice cream parlors, and more.
Find more great Long Island towns in our Guide to the Best Towns on Long Island.
Subscribe to our newsletters to get stories like this delivered directly to your inbox.
Cute Towns With Walkable Main Streets in Nassau County
Farmingdale Village ranks high on the walkability scale with its centralized restaurants and shops. Main Street is the town's hub for annual cultural events, and there are tons of kid-friendly restaurants.
Best Things To Do With Kids: The annual Music on Main festival is a FREE annual event that closes Main Street and lets visitors enjoy live music and more. There is also an annual Memorial Day parade, and the Village Green is a hub of activity. In the fall, there’s Art in the Park, which celebrates its 10-year anniversary in 2021.
Standout Local Eats: A Farmingdale favorite, The Chocolate Duck, serves masterful cakes and chocolates.
Take a ride on the beautiful and historic Nunley's Carousel. Photo courtesy of Wikimedia Commons
Garden City is best known for its Museum Row, where you'll find The Long Island Children's Museum and the Cradle of Aviation Museum, two of our favorite kid culture spots on Long Island. Garden City has a bustling downtown that’s ideal for families ready to stroll the streets. Avoid driving and take the LIRR to Garden City: It’s about a 10-minute walk to Seventh Street and Franklin Avenue, Garden City’s hub.
Best Things To Do With Kids: Walk to the nearby Garden City Public Library and browse the children’s section. There's a great special-needs collection of books and an enchanting mural of Alice in Wonderland, Curious George, and Madeleine in the story time room. Summertime brings Friday Night Promenades, filled with food, live music, and children’s activities. For a combination of shopping and classes, visit Kidville’s boutique for irresistibly fun toys and birthday gifts. Everyone can unleash their creativity at Muse Paintbar, where children and parents paint masterpieces together. The Paintbar doubles as a restaurant.
Standout Local Eats: The Burger Spot’s made-to-order burgers and salads satisfy a hungry crowd.
Oyster Bay has it all, from beautiful beaches and lush parks to historic attractions and scenic countryside.
Best Things To Do With Kids: Theodore Roosevelt Memorial Park has tennis, handball, and basketball courts, children’s playgrounds, and winding paths that are perfect for a stroll with the family. It's also home to the annual Oyster Bay Oyster Festival, the East Coast’s largest waterfront festival (canceled for 2021). The residents-only Beekman Beach is the perfect place to cool off. If the kids are ready to do some of their own cooking, What’s Cooking offers cooking classes for children and adults. The Oyster Bay-East Norwich Public Library is a great place to peruse children’s books.
Standout Local Eats: Stop by the Bonanza Stand of Oyster Bay for a hot dog and homemade Italian ices.
Families gather at Northport Park as the sun sets on the scenic Northport Harbor. Photo by the author
Cute Towns With Walkable Main Streets in Suffolk County
Northport Village’s waterfront views, and the quaint shops and restaurants along its Main Street, make this town a joy to explore on foot.
Best Things To Do With Kids: Located at the end of Main Street, Northport Park and Cow Harbor Park have play areas, pathways, and benches, making it the perfect spot to enjoy the scenic harbor. Be sure to check out the John W. Engeman Theater’s spectacular productions for children. Northport has a robust farmers market from June through November, and fall brings the annual Cow Harbor Day celebrations, including a fun run, concert, parade, and more family-friendly fun.
Standout Local Eats: If your sweet tooth aches for nostalgia, order a scoop of delicious homemade ice cream at Northport Sweet Shop Luncheonette, family-owned since 1929.
This bustling town appeals to the fast-paced lifestyle of Manhattanites, and its proximity to great beaches draws those seeking a slower-paced, beach-town vibe.
Best Things To Do With Kids: Bubble Boutique & Learning Center, owned by Babylon native Jenny Dellafranca, is a cool children’s boutique that offers creative classes. Her Bubble East shop sells clothing and jewelry for mom and dad. Babylon Village Chamber of Commerce hosts tons of events throughout the year, like the summer's Block Party series. Its Beautification Society hosts an annual fair in September. Theatergoers flock to the historic Argyle Theatre with its robust children’s lineup. Built in 1803, the historic Conklin House offers an opportunity to explore the past, and Argyle Park is minutes from the village and has a playground, a waterfall, and lakeside trails open all year.
Standout Local Eats: Glen’s Dinette is a Babylon institution serving traditional breakfast and lunch items kids love.
Amid blue skies brushed with clouds, the Heckscher Museum of Art in Huntington welcomes visitors. Photo courtesy of Heckscher Museum of Art
Huntington Village is a family-friendly destination for daytrippers from all over Long Island, especially during the holidays and on weekends. The town has plenty of kid-friendly activities, from cool museums and shops to restaurants and play spaces. There are also lots of fun, annual holiday events the whole family can enjoy.
Best Things To Do With Kids: Heckscher Park and The Heckscher Museum of Art are Huntington highlights. The park is where many of the town's annual festivals are held, like the annual Long Island Fall Festival. The Heckscher Museum's two 55-inch touchscreens inspire children to create beautiful works of digital art. And finally, Heckscher Park’s play area is great for kids of all ages. Children clamor to peek inside Little Switzerland Toys and Dolls. Claytime, just off Main Street, invites the entire family to paint ceramic pieces, from hedgehogs to coffee mugs. The Paramount's live family shows delight young audiences with top-quality entertainment, and The Huntington Village Art Walk is an annual event the whole family will love.
Standout Local Eats: Munday's offers kid-friendly breakfast, lunch, and dinner items; the restaurant's charm kicks into high gear during the holiday season with its over-the-top decorations.
These days, Patchogue is more walkable than ever. Plus, the town's LIRR station is close to all of the restaurants, shops, and activities Patchogue Village offers.
Best Things To Do With Kids: Patchogue’s Shorefront Park is home to the annual Great South Bay Music Festival. The Patchogue Arts Council sponsors art events throughout the year. At the Patchogue-Medford Library, you'll find wonderful children's programming. Head across the street to the Patchogue Theatre for the Performing Arts, which has a rotating program of family shows.
Standout Local Eats: When hunger strikes, nothing beats the barbecue at Bobbique.
Port Jefferson's shorefront ice skating rink operates seasonally. Photo courtesy of Discover Long Island
Steeped in maritime history, Port Jefferson is one of two ports on Long Island with ferry access to Connecticut. Its 350-foot pier and pristine promenade along the shoreline are minutes from Main Street.
Best Things To Do With Kids: The Long Island Explorium celebrates all things STEM and is located in the historic Chandlery building in Port Jefferson. In the winter, The Rinx opens an ice skating rink in Harborfront Park. Soak up the maritime culture and history at the Port Jefferson Village Center and Bayles Boat Shop. As you walk the shoreline, you can’t miss Port Jefferson’s Instagram-worthy Big Chair. Rocketship Park is a fun diversion for toddlers and big kids alike. The Charles Dickens Festival, complete with Scrooge and Father Christmas, enchants Port Jefferson spectators every December. The town's Theatre Three offers a robust calendar for kids and even hosts sensory-friendly productions.
Standout Local Eats: You won't be able to walk by Roger’s Frigate.
Sayville's main street packs plenty of old-school charm. Photo courtesy of Discover Long Island
Most people think of Sayville as the jumping-off spot for Fire Island, but it's also one of Long Island’s most walkable villages. Sayville’s seasonal festivals in Gillette Park shouldn't be missed.
Best Things To Do With Kids: When the weather warms up, The Common Ground at Rotary Park features tons of fun events, like Family Fridays and Yoga in the Park. Sayville Falls Miniature Golf is beautifully maintained and scores big with families. Sayville Cinemas is a small, manageable theater with incredibly cheap tickets: $5 every day before 6pm and all day on Tuesdays. To find unique handmade gifts, toys, and gourmet items, visit the Sayville General Store, located in the historic Oysterman’s bank.
Standout Local Eats: La Tavola Trattoria serves traditional Italian fare in a cozy indoor dining room and on the beautiful outdoor patio.
East Hampton is home to plenty of local amenities and incredible natural beauty. Photo courtesy of Discover Long Island
Cute Towns With Walkable Main Streets on Long Island's East End
Though the Hamptons are best known as summer destinations, East Hampton’s Main Street is easily enjoyed year-round.
Best Things To Do With Kids: The 24-acre East Hampton Village Nature Trail is just a short walk from Main Street and is a great spot for birdwatching. Petit Blu toy store has a fine selection of children’s apparel and imported toys, as well as fun events during non-COVID times. Stevenson’s Toys & Games carries nostalgic and modern toys, and gift wrapping is complimentary here. East Hampton’s rich history is kept alive by the East Hampton Historical Society. Finally, if the weather isn't cooperating, nothing is better than a tub of popcorn and a movie with the family—Regal UA East Hampton is located right on Main Street.
Standout Local Eats: Sam’s Bar & Restaurant is family-run for three generations and perfect for families ready to tuck into pizza and Italian fare.
A favored historic North Fork village, Greenport is perfect for taking a family stroll. Greenport's walkable streets offer stunning waterfront views of Shelter Island and the Peconic River.
Best Things To Do With Kids: Children who dream of being a train engineer, firefighter, or sea captain will love the Railroad Museum of Long Island, Fireboat Fire Fighter Museum, and East End Seaport Museum, which are open seasonally. At nearby Mitchell Park, children can run around and cool off under the misters. Tucked away next to the Schoolhouse Museum is the Village Blacksmith Shop; on weekends, there’s a blacksmith hard at work. Burton’s Bookstore has a dedicated children’s section, and events include book readings from children’s authors. Goldsmith’s Toys & Electronics' rubber ducky collection and toys are a sight to behold. The Northrup-Grumman Carousel was built in 1920 and houses 36 jumping horses (18 of which are hand-carved) and two sleighs to choose from. The much anticipated annual Maritime Festival celebrates local maritime heritage with delicious foods, local vendors, and activities.
Standout Local Eats: Claudio’s has several options: Families can dine at Claudio’s Waterfront, Claudio’s Restaurant, Crabby Jerry’s, or Claudio’s Pizzeria.
There's nothing but sun and smiles at Montauk’s breathtaking Kirk Park Beach. Photo by Stephanie Garrett
Located at Long Island's easternmost point, Montauk has something every member of the family will love.
Best Things To Do With Kids: White's Drug & Department Store is Montauk's premier spot to shop for a variety of gifts and essential items. The Historical Society’s Second House Museum is Montauk’s oldest structure. Though the house is currently closed for restoration, Montauk’s annual craft fair takes place on the grounds. Explore indigenous Montauk culture and history at The Montauk Indian Museum. For the most scenic game of miniature golf, head to Puff & Putt Family Fun Center. Kirk Park Beach is minutes from Montauk's Main Street, and the smooth sand, crashing waves, and open ocean are what make Montauk special.
Standout Local Eats: Don't miss Montauk Bake Shoppe's irresistible jelly croissant—it’s a must.
Children revel in up-close animal encounters at the Long Island Aquarium. Photo courtesy of Long Island Aquarium
Riverhead is a child’s adventure waiting to happen with kid-friendly attractions like the Long Island Aquarium and the nearby Splish Splash Water Park.
Best Things To Do With Kids: The Long Island Aquarium has garnered nationwide recognition, and its more than 1 million gallons of water are contained right in the heart of the Riverhead. Learn more about liquids and gases at the Long Island Science Center, which plans to increase its footprint on Main Street. Summertime heats up with Alive on 25, which includes fireworks, a classic car show, activities for kids, vendors, food trucks, and, of course, live music. The town's annual Halloween Fest packs downtown Riverhead with fun costumes and all-ages activities.
Standout Local Eats: Why not give in to temptation and try a hot, everything bagel at Goldberg’s Famous Bagels.
Originally published in 2019.
Places featured in this article: