Snooze, Booze and Diffuse in Historic Greenport

Ouside View of Ruby's Cove B&B

Located only two hours away from NYC, Greenport Village offers a fabulous summer escape for the weary New Yorker in need of a weekend holiday. If visiting this pretty and walkable historic coastal town on Long Island’s North Fork, be sure to check out (or rather, check-into) one of its most comfortable and unpretentious B&B joints, Ruby’s Cove.

The Digs.

Perched majestically on the corner of Carpenter Street and Bay Ave, and conveniently located “127 steps from Main Street,” is Ruby’s Cove Bed and Breakfast. From the outset, this B&B’s too-adorable outdoor wraparound porch, spring blooms and plush seating sets a relaxing tone, especially in the warmer season.

Ruby's Cove Outdoor Seating
Photo Credit: Ruby’s Cove Bed and Breakfast

Inside, Ruby’s Cove is carefully decorated with an eclectic mix of estate pieces, aromatic scents and little touches of beach decor.  Ella Fitzgerald music sets the ambience of the cozy ground floor parlor. For sure, this homey Victorian B&B exudes an air of grandiose 1930’s speakeasy flare. And much like its owner and operator, Ruby’s Cove is welcoming and accessible with a touch of sass.

Ruby's Cove Sitting Area
Photo Credit: Ruby’s Cove Bed and Breakfast


Feeling like sleeping in? Accommodations upstairs include three well-appointed guest quarters boasting original Victorian windows and antique pine floors.  Unsure about which room to select? Each space offers a different mood: Romance and love in the soft pink Madeline; Relaxation and peace in the nautical-themed Ballast; and Cozy comfort in the smaller, but aptly-named “Divine” quarters.

Ruby's Cove Accomodations: The Ballast
Photo Credit: Ruby’s Cove Bed and Breakfast

Convenience and comfort come standard! Think luxurious beds, fully decked with down-filled comforters and ultra soft pillows that offer delightful slumber for the restless.

Onto the Breakfast!

Offered at 10:00AM (sorry early birds!) breakfast is made by the owner herself and is usually accompanied by a great, big smile and delightful chatter with fellow guests. Request the mouthwatering coconut and peach pancakes to wake up the senses, or, opt for the fluffy chili and egg casserole to hit the spot!

Ruby's Cove: The French Toast
Photo Credit: Ruby’s Cove Bed and Breakfast

Oh, if you ask nicely (and in advance), the signature French toast and berries platter will be served for breakfast. Prepare for a feast.

Ruby's Cove Dining Room
Photo Credit: Ruby’s Cove Bed and Breakfast

At this B&B, the food is served hot, rich, delicious and in generous proportions.

Ruby's Cove: Snacks and Sweets
Photo Credit: Ruby’s Cove Bed and Breakfast

And in case you’re looking for a quick nibble or refreshment, not to worry. Throughout the day, local beer, wine, tea and pastries are available for general consumption.

Attractions and Adventures.

When you’re done noshing on delish breakfast fare, burn the calories you’ve just consumed and take advantage of the complimentary bicycle rentals offered at Ruby’s Cove. Be sure to take a spin around Greenport’s quaint downtown (and beyond!) to get the best out of your trip. Area attractions include dozens of unique local wineries (Kontokosta Wineries); local harbors; beautifully curated art galleries; quirky specialty shops; and even a beer brewery in town (Greenport Harbor Brewing Company).

Greenport Attractions
Photo Credit: Donna Gruber

Photo Credit: Donna Gruber
Photo Credit: Donna Gruber

Love the natural landscape? Be sure to check out the gorgeous, cliffside local beaches, which are perfect for sunset watching; ride a subsidized ferry to secluded Shelter Island for an exciting hiking adventure; or just sit around the awesome dockside public plaza downtown, suitable for chill-axing and equipped with a vintage carousel merry-go-round for you…AHEM…the kids!

Greenport Attractions: 67 Steps Beach
Photo Credit: Donna Gruber

This place offers just plain, low key relaxation. Do. Not. Miss. Out.

Eating Out and Hanging About.

Curious about outside dining options? Not to worry. Especially in the warmer months, Greenport scores high in terms of dining out and the late night scene, with soulful restaurants like First and South, more relaxed fare from the local North Fork Food Truck and evening fine dining (minus the snobbery) at the trendy and tres-chic Frisky Oyster.

Greenport Restaurants: First and South
Photo Credit: First and South Restaurant

In the afternoons (or whenever!) try the delicious baked goods and ice cream at local spots like D’latte Cafe and Gelato and The Market: Whole Foods & Supplements Cafe, where your  tastebuds will surely not be disappointed.

Greenport Restaurants Snapshots: First and South
Photo Credit: First and South Restaurant

Greenport will definitely meet your night scene and dining out needs  –  from its fully-stocked bars to live music and a selection of excellent seafood dishes, the options are abundant.

Pro Tips:

(1) Not driving in on your own? Then hop on the Hampton Jitney from Manhattan for a comfortable  and relaxing bus ride into town. During high season in the warmer months, opt for the Long Island Rail Road instead to avoid the inevitable traffic jams.

(2) Looking for more sights, tastes and sounds outside of Greenport and in the general North Fork area? Sign up for a fantastic and thorough tour of local vineyards a-la-Jo-Ann with Vintage Tours. Expect to be very well informed, well fed, and a little boozed up.

When to go:

It all depends on your interests! Mid-to-late September if you’re going for grape harvesting season and the seasons’ newest wines (and for fresh farmers market cheeses, pumpkins and apple-picking!); in the winter for a cozy retreat and mulled wine; in the warmer summer months if your scene is all about live music at the wineries (and for the option to take a dip in the Long Island Sound or Peconic Bay).

Free yourself from the dog days of summer in Greenport, a surprisingly happenin’ gem of a small town, and be ready to unleash your inner cool.  And remember to stop by Ruby’s Cove for a comfy stay for your fun and play!

Olga Abinader proudly hails from a family of Caribbean and Middle-Eastern self-taught culinary experts. Her rich heritage inspires her to pursue all things creative and remain curious about culture, food and travel. A fanatic of urban places, Olga's profession is in urban planning and design in the New York City metro.

Be first to comment

Leave a Reply