Return to Blog

Apr Seasonal Getaways: Spring on Long Island

Spring is the perfect time to explore Long Island. Here on the East End, there are so many sights and sounds to stimulate your senses. The North Fork, with over 60 wineries & breweries and a rich maritime history, is a great place to relax and indulge your palate. The South Fork, with its iconic lush vegetation lining winding roads dotted with cedar-sided buildings is the place to see and be seen.

The entire east end of Long Island can be covered leisurely in a long weekend. Here’s our guide for hitting the best spots of the east end and getting the most out of the season.


Long Island’s North Fork: Unique Wine, Craft Beer and Rich Maritime History

The best place to start exploring the East End is the North Fork. By starting early, on a Friday morning for example, you’ll miss all of the traffic on the narrow North Fork roads. We suggest driving out to Greenport first, which is near the end of the North Fork, and making your way back inland by stopping at wineries and breweries along the way. Here are our picks for Spring:

Lunch at Claudio’s

Offering fresh seafood and other local Long Island fare, Claudio’s has been a staple in Greenport since opening its doors in 1870. This place plays a big role in Greenport and Long Island’s maritime history, so be sure to check out the historic photos adorning the interiors of the charming restaurant. Each table offers views of Greenport harbor and Shelter Island across the bay. If you’re curious to learn more about Greenport’s maritime history after your meal, the East End Seaport Museum is just a short walk away.


Stroll Downtown Greenport

Downtown Greenport, situated near the end of the North Fork, is a quaint collection of shops, restaurants, and attractions. One our of favorites, Vines & Branches, is an artisan goods shop where you can taste over one hundred different types of olive oils and balsamic vinegars. In Mitchell Park across the street, you’ll find the historic Herschell-Spillman carousel dating back to 1920. It’s open for $2 rides from 10:00-6:00 on the weekends.


Sparkling Pointe Vineyards & Winery

For those who like bubbly, this place is for you. Carefully selected clones of Pinot Noir, Pinot Meunier, and Chardonnay varietals lend to excellent vintages of sparkling white wine. The tasting room at Sparkling Pointe is gorgeous, offering well-appointed indoor and outdoor spaces. Also offered are cheese pairings and other complementary small plates to enjoy with the wine and beautiful vineyard views.


Greenport Harbor Brewing Company

Greenport Harbor Brewing Company is a true gem of the North Fork. The brewery’s Otherside IPA is so popular at Madison Square Garden in NYC that the company can’t keep up with demand. Check out their recently relocated headquarters in Peconic and enjoy a flight in the quickly-expanding open air tasting room.

Bedell Cellars

Another North Fork winery not to be missed is Bedell Cellars. Growing 17 grape varietals over three plots on Long Island, the lineup is diverse with flavor profiles. One of the first vineyards in Long Island, Bedell has a rich history and deep knowledge of the Long Island geology and climate; lending to excellent winemaking. The large, airy space has a Long Island feel with white wood throughout and offers both indoor and outdoor wine tasting.

Dinner at Bistro 72

After spending the day driving the North Fork, enjoy a meal of local cuisine at Bistro 72. Bistro 72 sources ingredients from over 15 Long Island sources, many of which are on the North Fork. Many local wines and craft beers are also on tap here, so use your newly-acquired knowledge and create your own pairing! We suggest Twin Fork Beer Co’s Chromatic Ale with Bistro 72’s Eastern Long Island Steamed Mussels. Yum!

If you’re a guest at Hotel Indigo, check with the front desk for the hotel shuttle’s availability. It is available on an on-call basis to safely transport you around Riverhead for a night on the town. Downtown Riverhead is experiencing a resurgence, with fun nightlife on Friday nights at places like Vines & Hops. Crooked Ladder Brewing Company is also located in historic downtown Riverhead, and Long Ireland Brewing Company is nearby.


The South Fork: Hamptons Opulence, Luscious Landscape and Sweeping Ocean Views

Spend a Saturday cruising the Hamptons. The scenic drive along the South Fork is filled with sweeping vistas of the ocean accompanied by shores lined with dunes and picturesque homes. Further inland, you’ll find the roads lined with cedar-sided buildings and homes against the backdrop of lush evergreens.

Breakfast at Star Confectionery in Riverhead

Begin your South Fork trip with a satisfying breakfast at Star Confectionery. The restaurant, established in 1911 and located in Riverhead, is famous for their ice cream and homemade chocolate. However, they serve a delicious counter-style breakfast to start your day.


Westhampton Dunes & Beach

Cupsogue County Park, at the very end of Dune Road in Westhampton Dunes, is a beautiful starting point for a drive through the Hamptons. With ample space for parking, it’s easy to hop out and enjoy the beach for the afternoon or just for a short stroll beside the ocean. Along the drive here, be sure to check out the picturesque homes lining the coastline.

Stroll downtown Southampton

Downtown Southampton is the place to see and be seen. The streets are lined with unique vintage storefronts selling goods from artisan foods to high-end clothing. At the north end, be sure to stop in world-famous Tate’s Bake Shop. Known for their crispy chocolate chip cookies, Tate’s Bake Shop has a large selection of confections like shortbread cookies and freshly-baked blondies.

Leisurely Drive through Bridgehampton

The drive along Route 27 is a scenic one, showcasing densely forested backdrops and iconic cedar-sided buildings accented by chalk-white trim. Driving through – windows down – is the best way to get a good overview of daily life in the Hamptons as you pass historic post offices and schools and take in the fresh air fragrant with the sweet smell of evergreens.

Late lunch at Bostwick’s Chowder House in East Hampton

A place where it’s ok to be casual, Bostwick’s Chowder House offers a wide array of seafood staples alongside daily chalkboard specials. The crab cakes and lobster roll are our favorites. Of course, they also offer several varieties of chowder from clam to corn!


Visit Montauk Point & Montauk Brewery

Montauk Point, at the very tip of Long Island, offers sweeping ocean views and the oldest lighthouse in New York state. You can also walk along the rocky shoreline. Parking at the state park for a single vehicle costs $8. On your trip back inland, stop by Montauk Brewing Company for a flight of beer. The handsome tasting room offers both indoor and outdoor space.


Spend the evening in Sag Harbor

Sag Harbor is a great place on the South Fork to relax for the evening. The adorable downtown offers many eateries and storefronts to stroll by and people watch. If you’re hungry, celebrity chef Laurent Tourondel’s LT Burger is great for gourmet burgers in a sleek space. The iconic Sag Harbor neon sign, right downtown on Main Street, is the perfect spot for a selfie!

Of course, you may not be able to accomplish everything on this list. If your interest is piqued, you may want to spend more time in one place and skip another. This list is designed for a two-day getaway with a vehicle.

Map of the following locations can be found here.

Claudio’s 111 Main Street, Greenport

Vines & Branches 110 Front Street, Greenport

Greenport Harbor Brewing Company 42155 Main Road, Peconic

Sparkling Pointe 39750 County Rd 48, Southold

Bedell Cellars 35225 Main Road, Cutchogue

Bistro 72 1830 West Main Street, Riverhead

Star Confectionery 4 E Main St, Riverhead

Cupsogue County Park 906 Dune Rd, Westhampton Beach

Tate’s Bake Shop 43 N Sea Road, Southampton

Bostwick’s Chowder House 277 Pantigo Road, East Hampton

Montauk Point State Park 2000 Montauk Hwy, Montauk

Montauk Brewing Company 62 South Erie, Montauk

LT Burger 62 Main Street, Sag Harbor

For more information or to reserve a room for your Long Island getaway, contact Hotel Indigo at 631.369.2200 ext. 0. We look forward to seeing you on the East End this Spring!