Ah, the Gold Coast. Where winding ribbons of asphalt thread otherwise unspoiled hills. It’s summer, roll down the windows, drop the top if you can and point your wagon toward 25A, where the season greets you with sea breezes. Culture, shopping and restaurants thread together picturesque port towns and historic, stunning homes (some of which are open to the public).
Town: Port Washington
Hit Port Washington on a clear, sunny day and prepare for a clinic in port town living.
Start by the town dock on Main Street and head up the hill to take in all the scenery and unique boutiques (there will be more of this, wear comfortable shoes). Where Main Street meets Shore, you’ll notice a restaurant dead ahead with a patio commanding an elevated view of the street below and the port beyond. This is Ayhan’s Mediterranean Marketplace Cafe, a good stop for catching up with a book over lunch.
Eat lightly however, because the trek up the hill continues shortly. Where the sidewalk winds behind the massive public library, take a break if needed under the shade of the old growth linden tree. This is the halfway point. Check the lineup at Landmark on Main Street, stage of folksy singer-songwriters (Roseanne Cash), Broadway divas (Christine Ebersole) and roots, jazz and rock (Buckwheat Zydeco). You’ll want to come back here.
At the top of the hill, find Blumenfeld Family Park. If you brought the kids and if they brought their swimsuits, set them loose at the water park at one end of the wide, curving pathway. Pick any one of the numerous old growth trees that dot the open space and finish that book you started at lunch.
For a more in-depth nature experience, hop back in the car and head south for Leeds Pond Preserve where trails wind around hills, vales, trees and a trickling stream that invites a moment of reflection.
Feel like swinging?
Port Washington’s Harbor Links boasts award-winning 18-hole play, instruction and mini golf.
If this downtown had not been carved out of a long, sloping hill over centuries, you’d swear it was engineered to coax every drop of quaint out of the waterfront. The way the towering spire of the Edward Thompson Co. building looms over a sprawling grassy field that stretches toward Long Island Sound, the way a streetcar line bisects Main Street and meanders down to a park, the way back alleys lead to wide courtyards dominated by bubbling fountains and ivy, it all seems too perfect.
It’s a small wonder that Jack Kerouac settled here after famously criss-crossing the country. You could travel the world and not find a place that felt more like home.
Speaking of the beat poet, his favorite haunt, Gunther’s, still stands exactly as it did during his heyday (it even still has—get this— a payphone). Stop in for a quick drink or five and check out some Kerouac memorabilia. Be sure to ask about the time they parked a motorcycle inside the bar. Or beg to see the Prohibition era tunnels that lead to the waterfront.
The small-town bliss continues down the street at Tim’s Shipwreck Diner with buttery pancakes and superb coffee (until 3pm!). Walk through a small corridor and find their surprisingly open courtyard. This ivy-strewn oasis is one of Northport’s hidden gems. The restaurant happens to share this courtyard with Maroni Cuisine around the corner. Maroni offers up some life-changing Italian food in a 20-seat restaurant. The recipe for meatballs is almost a century old, which proves that when you get it right once you never have to change.
Town: Port Jefferson
There’s an odd function of tourist-driven coastal towns that they must always have one of each of the following: A store selling pirate memorabilia, an ice cream store, a fudge shop, a coffee house, a store selling hand-crafted wooden toys.
You can go from New Orleans to Savannah to, San Francisco and see those same five shops. So what makes Port Jefferson so special?
It’s a tourist-driven coastal town that doesn’t feel like a tourist-driven coastal town. When the horn blasts for the Connecticut ferry and the traffic streams up Main Street, you realize this is a fully functional downtown that just happens to have some tourist spots scattered around it.
But you can’t blame summer revelers flocking to Port Jeff. While there’s not necessarily a boardwalk, there’s still plenty to take in within walking distance. If you’ve brought the kids along, treat them to a belly full of fudge, ice cream, candy and numerous other treats at The Port Jefferson Frigate, the wide front porch of which dominates the water front. It’s the one with the giant ice cream cone, you can’t miss it.
If you left them at home, enjoy a relaxing spa day at the The Blue Sapphire Spa, a romantic waterfront dinner at WAVE Seafood Kitchen or a flight of local craft beer at Port Jeff Brewing Company.
Or, just walk the main street from the top of the hill down and pop into a bevy of shops, dining spots and attractions. There’s more than you can see in a day, take a leisurely pace and plan on returning.
NORTH SHORE CHECKLIST
Go shopping at Americana Manhasset, home of 60 deluxe boutiques framed by unique landscaping and architecture.
Drive 25A, the Long Island Heritage Trail, and soak in the ambiance of the Gold Coast.
Tour the historic homes of American luminaries like Walt Whitman, Teddy Roosevelt and the Vanderbilts.
Write a poem about it all later.
ON THE NORTH SHORE THIS SUMMER:
Summer Splendor, Northport: A self-guided tour of some of the splendid private gardens in and around Northport.
Theatre Three, Port Jefferson: Sizzling Summer Concert Series plus Dramatic Academy runs throughout the summer with Mainstage performances every Friday and Saturday.
Midsummer Night Dances at the Vanderbilt Museum, Centerport: Dance lessons every Thursday night. Also at Vanderbilt expect drumming circles, live painting and Grateful Dead fests.
Summer Arts Festival, Heckscher Park, Huntington: The outdoor summer concerts take to the Chapin Stage all summer long and range from jazz to comedy.