Long Island Towns: Riverhead

Riverhead, known as the “Gateway to the Forks,” is rich in agricultural heritage and early American history. Named by Forbes as one of the Top 50 Travel Destinations in 2023, the town is home to farmlands and the entrance of Long Island Wine Country, world-class entertainment and attractions, and walkable streets lined with historic architecture and landmarks that reflect the region’s 18th and 19th century roots. The town of Riverhead includes the hamlets of Aquebogue, Baiting Hollow, Calverton, Jamesport, Laurel, Manorville, Northville, Riverhead (the hamlet), and Wading River.

Spend the weekend exploring all that Riverhead has to offer. We rounded up some top spots for your Riverhead itinerary:

Morning:

Hike & Shop

Right photo credit: @longislandaquarium on Instagram

Riverhead sits where the North and South Forks split with the Peconic River running through town, making it a prime location for kayaking, canoeing and boating. Plus, there isn’t a shortage of public parks to explore the different landscapes of the region. Start your day out in nature at Cranberry Bog County Park, David A. Sarnoff Pine Barrens Preserve or Hubbard County Park. For beach vibes, head to Indian Island County Park or Reeves Park Beach. Live like a local and pack a BECSPK (bacon, egg, and cheese with salt, pepper, and ketchup) and North Fork Potato Chips from a local deli for breakfast at the park.

Come back to Main Street and learn Riverhead’s rich history by walking the Downtown Riverhead Historic Trail. Use your smartphone to view the map, and at each stop scan a QR code. You will then hear a first-person narration by a historic character associated with that place and see archival images.

The historic trail will take you down Main Street and around surrounding streets, leaving the perfect opportunity to blend history with shopping the local boutiques and storefronts with everything from artisan crafts to clothing to jewelry.

Afternoon:

Cheers to Local Flavors or Fun with the Fam

Riverhead

The North Fork extension off of Riverhead is home to the award-winning Long Island Wine Country, where acres and acres of vines account for over 60 wineries that stretch all the way to the easternmost of the North Fork, however you can still find that taste of wine without actually leaving Riverhead. The region has a similar maritime climate to the classic Bordeaux Region of France, fostering an environment where winemaking thrives. Most vineyards allow walk-ins, but be sure to call ahead and make a reservation if you’re traveling with a large group. Choose from these wineries:

Palmer Vineyards: One of Long Island’s oldest vineyards. Pet-friendly and laid-back vibe. Serves charcuterie boards, pretzels and pizza, all perfect for wine pairing.
RGNY: Family-owned and operated and celebrates its Mexican roots. Seasonal fare and a lively, popular brunch every Sunday with live music, a full menu, flowing wine, and churros.
Terra Vite Winery & Vineyards: Amalfi Summer meets old world Italian chic. Wide shareable food menu.

If you’re more into beer, don’t fret. Eat lunch and taste local flavors at Riverhead Brewhouse, known for the seasonal, rotating draft list of 24 beers, handcrafted cocktails and mocktails, large plates and juicy burgers. Or head to Jamesport Farm Brewery, where you can fill up on tasty choices from on-site food trucks and enjoy ice-cold beer. Jamesport Farm Brewery is Long Island’s only true farm-to-pint brewery. The farm supplies nearly all its own fresh hops, barley and wheat used in the brewing process.

In the fall, don’t miss a visit to Harbes Orchard, whose season begins Labor Day Weekend, for a classic apple picking straight from the trees, then head over to Riverhead Ciderhouse, open year-round, for homemade cider, live music, and board games. Sticking with the rural vibes, Waterdrinker Farm has a location in Riverhead, perfect for some family fun.

Riverhead

Focus on Riverhead’s history and participate in a guided tour at the Hallockville Museum Farm, where visitors can explore the property and learn hands-on about the way that early pioneer farmers lived in the 18th century. The property contains 28 acres with 19 historic houses, barns and outbuildings ranging from the mid-18th century Hallock Homestead to the Depression-era Cichanowicz Farmhouse.

Prefer an indoor activity? The Long Island Aquarium entertains all ages. Take a selfie with a penguin, high-five a sea lion, dive with sharks and see thousands of fish from all over the world.

Evening:

Dinner & A Show

Riverhead

The Suffolk Theater on Main Street first opened its doors in 1933, and still celebrates the performing arts today. Catch a show during your trip and take a picture in front of the iconic art-deco marquee.

Afterwards, snag a table at locally-loved Jerry & The Mermaid for a casual, fresh seafood dinner near the water. Try Jerry’s Famous Lobster Roll or the Sesame Crusted Ahi Tuna.

While You’re in Town:

Bottom photo credit: @hyattplaceeastend on Instagram

If you have extra time (or you aren’t ready to head home yet) these local gems are well worth the detour off Main Street.

Golf– Cherry Creek Golf Links | Woods at Cherry Creek | Indian Island Golf Course

Splish Splash– Summertime fun for all ages, Splish Splash has waterslides, rides, wave pools and more. Located next door in Calverton, it’s the largest waterpark in the tri-state area!

Lavender by the Bay Calverton– Frolic through the sea of purple and buy lavender products every year while the fields are in bloom.

The Big Duck– Stop by this odd roadside attraction while in Riverhead. The Big Duck is a 20-foot tall duck-shaped building in Flanders, worth the pitstop.

Getting There:

While driving offers flexibility, parking in Downtown Riverhead can be limited during peak hours and weekends. Public transportation via the Long Island Rail Road to Riverhead Station on the Ronkonkoma line makes it easy to visit without a car. Plus, ride share options (Uber/Lyft) and local taxis can help you get around.