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How to spend a family-friendly day in Greenport 

There are a lot of family-friendly things to do while visiting Greenport, which remains one of Long Island’s great summer destinations. Credit: Corey Sipkin

Family fun doesn’t have to mean traveling far. Greenport is one of Long Island’s popular summer destinations, offering an escape that doesn’t have to last longer than a day trip. Here are family-friendly ways to spend the day in the village.

GETTING THERE

If you choose to drive, there are free parking lots downtown. Parking is also available on Front and Main streets; it’s timed at two-hour limits. The final LIRR stop on the North Fork is Greenport, from which the village is footsteps away. Know that you’ll need to wear a mask. Posted signage in the village state face masks are required at all times, inside or outside, on docks, beaches, parks and other destinations.

PARKS AND BEACHES

Mitchell Park: While the village’s go-to carousel is currently closed, the park (115 Front St.; 631-477-0248, villageofgreenport.org) remains a spot where kids can play and it’s dog friendly. Families can wander along the waterfront and watch boaters.

Arshamomaque Preserve: Located on the edge of Greenport, the preserve (920 Chapel Ln.; 631-765-5711) is a place where families can explore — just make sure you keep your dog leashed. Featuring 126 acres of wetlands and woodland habitats, look out for an abundance of wildlife. There are three short hiking trails (none are longer than a mile).

Orient Beach State Park: Beach time for visitors to the village is not a likelihood as, per posted Southold Town orders, parking is only allowed for people with residential permits until further notice. However, Orient Beach State Park (40000 Main Rd., Orient; 631-323-2440, parks.ny.gov) is about 10 miles east of Greenport. Capacity is currently being reduced. Cars pay $10 to enter. Located along Gardiner’s Bay, it has a large sandy-yet-rocky beach where people sit in the sun while others fish. There are nature trails; the park is a great place to bird watch, and kayaking is permitted.

HISTORICAL SIGHTS

Walking tours: Greenport has many tales to tell. A walking tour of the village’s historic district can be done anytime; just visit greenportvillage.com and download the directions for free. There are some preserved buildings used for historical purposes, like the Greenport Jail and Police Museum (232 Carpenter St.) and the Old Kindergarten Schoolhouse (101 Front St.).

Railroad Museum of Long Island: The Greenport museum (440 4th St.; 631-477-0439), which exists inside the defunct LIRR Greenport Freight House, is closed for the season. But outside, there are vintage train cars to see for free, including a 1927 caboose and a former LIRR snowplow built-in 1915 from an even older flatcar, before being rebuilt in 1978 (and festooned with cartoon fangs and the name “Jaws III”).

ACTIVITIES        

Skate park: The village skate park (villageofgreenport.org) is open, featuring ramps, a half-pipe and other items on which to trick. Safety gear and helmets are required. Open dawn to dusk.

Mini golf: Golf at Drossos Motel (69125 Main Rd.; 631-477-1334, drossosmotel.com) is open to the public daily. The course has 18 holes and features the Jennie’s at Drossos snack bar (jenniesatdrossos.com).

SHOPS

Greenport is a very walkable town, with much of what can be shopped on Front Street between Third Avenue and Main Street, and then on Main between its south end (by Claudio’s) and Center Street.

Goldsmith's Toys & Electronics: This shop (128 Main St.; 631-477-0466, greenportvillage.com/goldsmiths-toys-and-electronics) has direct appeal to kids. Walk past and see the rubber ducks in the window — it’s the store’s signature item — but walk inside to find a variety of toys and seasonal fun; it’s an independent toy store that’s been in town for more than 30 years.

Sweet Indulgences: It’s also highly likely your little one digs treats, so a stop by this shop (200 Main St.; 631-477-8250) should not disappoint. Parents can peruse the many home décor items for sale, while also finding lots of candies and chocolates.

One Love Beach (211 Main St.; 631-333-2064, onelovebeach.com) is another place that should have some youth appeal, as it carries beachy gear and summery clothes while also offering paddleboards and kayaks for rent.

OUTDOOR EATERIES

You won’t have a hard time finding food in this village, as there are several restaurants, ranging from fancy and upscale to simple yet scrumptious with family-friendly menus.

For Breakfast in town, there’s Bruce & Son (208 Main St.; 631-477-0023, bruceandsongreenport.com), which features an all-day opportunity to munch on some morning-centric dishes. As does Crazy Beans (2 Front St.; 631-333-2436, crazybeansrestaurant.com) which is currently advertising new specials including graham cracker-crusted French toast.

For lunch, one place that proves entertaining for young eyes is Lucharitos (119 Main St.; 631-477-6666, lucharitos.com), a taqueria that has colorful décor dedicated to Lucha libre wrestling as well as a kids' menu. Andy’s Restaurant (36 Front St.; 631-333-2525, andysgreenport.com) is also an option, with burgers and mozzarella sticks among the menu choices (as well as some dynamite French fries).

For dinner, you can swing by 111 Main St. and try Claudio’s Waterfront for a meal that goes down dockside and a menu that centers on seafood and pub grub — or visit its wharf-sharing sibling eatery Crabby Jerry's; the same kids' menu is served at both (631-477-0627; claudios.com). Front Street Station (212 Front St.; 631-333-2050, eatatfrontstreet.com) is also a classic area restaurant that’s family-oriented with outdoor dining.

Make sure to check out the NorthFork Cooks food truck parked behind First & South (100 South St., Greenport; 631-333-2200, firstandsouth.com) restaurant this summer. The spot has tranformed into a campsite-inspired courtyard to dine. Guests can order from the venue’s menu or from the food trucks list of dishes—and both can be served with cocktails, mocktails, wine, beer and spirits. Each of the yard’s socially distanced tables is equipped with a lantern, while Edison bulbs dangle overhead. Leashed dogs are permitted and chalk is given out to children so they can draw on the concrete path that runs through the lawn. There’s also a large outdoor movie screen and starting Aug. 1 films will be shown Wednesdays (for date nights) and Saturdays (for families) starting at sundown. A turntable spinning vinyl provides tunes, watch for pop-ups from indie filmmakers and live music plays 6 p.m. to 9 p.m. every first Friday of the month.

If the kids are looking for dessert, Greenport Creamery (142 Main St.; 631-333-2818, greenportcreamery.com) scoops homemade ice cream from a rotating and seasonal selection, while Ralph’s Famous Italian Ices (37 Front St.; 631-592-8391) is another fast way to get a cold and creamy snack when visiting the village.

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