Planning the Best Date Night Ever in Red Hook

Planning date nights is serious business.

It was a hot NYC day in August and it was my job to plan a surprise date night for my girlfriend and I.

Getting out of Manhattan was my first priority. Being close to water was second. Seafood third.
I was inspired by my friend Anna’s comprehensive list of recommendations for Red Hook. Neither my girlfriend nor I had been before, not even to the Ikea, a trip which has been known to make or break relationships.

Taking the Ikea Express NYC Water Taxi

My girlfriend and I hopped a subway to the Financial District to catch the (free-on-weekends!) NYC water taxi. I love NYC’s ferries, as they’re about as close to nature that a NYer can get without leaving New York (other than the parks, of course).  Once we hopped on the ferry, my girlfriend thought our surprise date-day was a trip to Ikea to buy me a shelf. I was pretty pleased at myself to keep this illusion going.

Needless to say, my girlfriend was extraordinarily happy when we stayed on the boat and proceeded to Red Hook. The moment we docked, I bee-lined for our destination: Brooklyn Crab Shack. I was on the verge of hangriness so my inner mantra was food-now-please-food-now-or-I-will-unleash-my-rage.

Get yer crabs at Brooklyn Crab

When we first arrived at Brooklyn Crab, we were like “uh oh, this place is packed”. I feared for my stomach sanity, but quenched our 20 minute wait with some delicious IPAs at the bar.

When we received a text saying they were ready to seat us, we meandered up the old wooden steps to the top floor, where Brooklyn Crab and its cozy, family-friendly and casual environs awaited us.

My friend, Sabrina, a self-described crab-enthusiast,from Maryland who can shell a crab shell like no one else, says it best when she writes, “if you’ve never had Maryland blue crabs then stop reading this and go to Brooklyn Crab!” So, this is a definite win.

My girlfriend did all the hard work — opening the crabs and pulling out insanely sweet crab meat. She claims that the “work makes it taste better”. This is great for me, because “working” for my food sounds like the worst thing ever.

We also split the Blue Crab Roll, which came with freshly cooked kettle chips and a pickle. In my humble opinion, the second best part of this roll (after the crab) is the roll. It reminds me of eating Wonder Bread when I was a kid. Chewy, airy and delicious.

A failed attempt at dessert

I really wanted to surprise my girlfriend with a Brookster, a miraculous creation consisting of a cookie inside of a brownie, so went to Baked. Unfortunately (take note!), Baked closes at 7:00pm on weekends and it was 7:03pm. #sniff.

A second (and defiantly successful) dessert attempt

BUT, all was not lost! Fort Defiance was nearby.

Fort Defiance is a quaint, hipster restaurant that is run with love. We split The Pundit, a coffee-infused Scotch, Cocchi Torino, and Amaro dell’Erborista, and Steve’s Key Lime Pie. Steve’s Authentic frozen key lime pie sticks are a local favorite. The frozen variety was not served here so we stuck with the traditional, and boy was it deliciously tangy, with a perfect graham-cracker crumbly crust. Even my girlfriend who claims to “hate key lime pie unless it’s really really good” liked it. Trust me, that means something.

It’s dark out and that means we can start drinking hard stuff

It was nearing 8:30pm and, for us, that was 2 hours before bedtime (yes, even on a weekend), so I wanted to surprise my girlfriend with a drink at a casual local dive bar called Sunny’s. But, that comes later. Because, as we were walking down Conover street, we happened upon a beautiful open bar encased by large windows. Botanica is nothing short of beautiful.  They served local Widow Jane whiskey from the whiskey + chocolate Cacao Prieto next door, which made me feel hip. I plan to visit Cacao Prieto another day for a whiskey flight and some dark chocolate.

Live music, anyone?

After a drink there, we went to Sunny’s Bar. A little aside: I’m Indian-American and grew up in a white suburb near Albany, New York. BUT, ever since my twin sister and I watched O Brother, Where Art Thou? when we were in middle school, we have LOVED bluegrass music (country, too, but thats another story). I don’t know the first thing about it, but I still love it.

When my girlfriend and I walked in at 9:30pm, we found a cozy place to sit and wait for the music to start. And, seriously it was magical. It felt like we were spectators in the living room of a bluegrass jam band. The band grew from 4 to 5 to 6 to 8 people. The women singers were especially on point. The owner of the bar is a singer and bluegrass musician herself. At one point, a guy was singing some song and the entire audience joined in. Made me wish I knew bluegrass a little better.

We rolled home at 11:30pm, WAY past our bedtime, but pretty damn happy. My girlfriend’s highlight: Blue Crab at Brooklyn Crab. My highlight: Bluegrass at Sonny’s. Go yourself and find your own Red Hook highlight.

Where to go

Brooklyn Crab
24 Reed St
b/t Van Brunt St & Conover St
Red Hook

Even though it was a failed attempt:
Baked
359 Van Brunt St
b/t Sullivan St & Dikeman St
Red Hook

Fort Defiance
365 Van Brunt St
b/t Sullivan St & Dikeman St
Red Hook

Botanica
220 Conover St
b/t Dikeman St & Van Dyke St
Red Hook

Sunny’s Bar
253 Conover St
b/t Reed St & Van Dyke St
Red Hook

Suma has also written about her favorite Indian food and coffee shop in NYC.