What to Know and Do in Brooklyn’s Most Expensive Neighborhood: A Cobble Hill Neighborhood Guide

Brooklyn Heights and Dumbo may be the Brooklyn’s most visited neighborhoods, but Cobble Hill is constantly topping lists as the borough’s most expensive neighborhood. Anyone have a spare $1.64 million? Because that’s the median price people spent on property in the neighborhood in 2021, according to Property Club. Luckily, you don’t need to have nearly that much to spend time in Cobble Hill, although participating in the best of what this Brooklyn neighborhood has to offer may take a sizable chunk out of your bank account. We’ll get into the top things to do in Cobble Hill in just a moment, but first let’s start off this Cobble Hill neighborhood guide with a little bit of background about the area.

Cobble Hill Neighborhood History

Cobble Hill is a relatively small neighborhood in the western part of Brooklyn, just south of Brooklyn Heights. It’s bound Atlantic Avenue to the north, Degraw Street to the south, Court Street to the east, and the Brooklyn-Queens Expressway to the west, although in reality, the neighborhood’s boundaries are actually pretty blurry, as Cobble Hill often gets lumped into a nebulous blob with Carroll Gardens and Boreum Hill. (The real estate industry likes to call this trifecta “BoCoCa,” but just like the word “fetch,” they should stop trying to make BoCoCa happen. It’s not going to happen.) But it makes sense as these neighborhoods have similar vibes and a similar history.

As is the story of the rest of New York City, after being home to the indigenous people for thousands of years, the area we now know as Cobble Hill was settled by the Dutch in the 1640s. The area was pretty rural until the first rowhouses were built there in the 1830s, starting the area’s transformation into a middle class neighborhood. Early twentieth century Cobble Hill (which wasn’t officially called that until the 1960s) was a neighborhood that had a strong Italian, Irish, and Middle Eastern presence, but like much of the city, it saw many of its residents decamp to the suburbs post-World War II. The brownstones left behind were scooped up by young professionals who saw the opportunity for cheap housing even if it meant putting in some elbow grease to restore these homes. Residents led the push to get the area designated a historic district in 1969 and continuously have fought against new developments that don’t seem to fit in with the cozy yet upscale character of the area. For better or for worse, with its historic district destinction and its eye-wateringly high housing prices, the Cobble Hill of today seems like it has reached its ultimate form, which is probably nice if you’re a young upper middle class family with lots of desposible income.

The Top Things to Do in Cobble Hill

Fill your camera roll with photos of brownstones.

Cobble Hill is a prime example of a brownstone Brooklyn neighborhood. Most of the housing stock was built before the 1930s, and with much of the neighborhood being designated a historic district, these beautiful row houses along tree-lined streets are here to stay. Speaking of historic, keep an eye out for these storied buildings in the neighborhood: Christ Church (326 Clinton Street), DeGraw Mansion (219 Clinton Street), the homes on Verandah Place, and innovative philanthropist Alfred T. White‘s Workingman’s Cottages and Tower and Home Buildings. The articles linked can probably tell these places’ stories better than I can.

Eat your way down Court Street.

I know that nearby Carroll Gardens’ Smith Street is considered the area’s Restaurant Row, but since the focus of our trip is Cobble Hill, make sure to visit the neighborhood’s main artery, Court Street. You’ll find plenty of dining options, especially if you’re willing to splurge, but my personal favorite is Shelsky’s of Brooklyn (141 Court Street). Other local favorites include The Chocolate Room, Court Pastry Shop, and Caputo’s Bake Shop.

Shop your way down Smith Street. 

I know I just said that Cobble Hill is the focus of this trip, but it’s nearly impossible to go to Cobble Hill and ignore nearby Smith Street, which runs through Boreum Hill and Carroll Gardens, depending on who you talk to. This lively commercial street is full of small businesses that cater to a bougie yuppie crowd. You’ll find gift shops like Exit 9 Emporium, vintage clothing and furniture stores like Unearth Vintage, historic businesses like Paisanos Butcher Shop, and community hubs like Books are Magic, not to mention an abundance of restaurants, as this is Brooklyn’s Restaurant Row. See how long you can hold out without blowing your budget.

Visit the New York Transit Museum.

This museum is a few blocks outside of the boundaries of Cobble Hill, but you might as well stop there if you are in the area. As the museum’s name suggests, here you’ll learn the history of NYC’s system of trains and buses. The exhibits are informative, but the highlight of the museum is the fleet of vintage subway cars on display. Also, be sure to stop by the gift shop, which has a great selection of transit-related reading material, as well as MTA-themed bric-a-brac.

Reflect on Revolutionary War history at Trader Joe’s.

Cobble Hill’s Trader Joe’s (130 Court Street) is unusual for multiple reasons. The first reason is that it’s located inside a stunning Florentine Renaissance building that used to be the Independence Savings Bank. With the store’s arched windows and chandeliers, this is one of the fanciest grocery stores you’ll ever visit. Second and more importantly, this Trader Joe’s is unusual because it is on the site of what was the area’s namesake, Cobble Hill. But Cobble Hill was long flattened by the British during the American Revolution, when they learned that George Washington used the hill to track their whereabouts. Today, an aged plaque on the front of the building commemorates that moment in history.

I hope you enjoyed this introduction to Cobble Hill, Brooklyn’s most expensive neighborhood. What other places would you recommend adding to this Cobble Hill neighborhood guide?

But before you go, if you liked this Cobble Hill neighborhood guide and you like what I do here at Shiloh in the City and want to continue getting to know New York’s history, culture, and things to do with me, sign up for my email list and follow me on social media. Thanks for reading!

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