The Sag Story
Sag Harbor was a major whaling and shipping port in the 19th century, so there’s no shortage of monuments, plaques, museums, burying grounds and other historic sites that illustrate its history.
One plaque on East Water Street (now Bay Street) explains that in Whaling's heyday - 1800-1850, the street bustled with warehouses, coopers and shipyards; ropewalks for producing ship’s riggings; tryworks for boiling down whale blubber into oil for lighting and lubricating; storehouses for whale oil and whalebone – all industries related to the maritime trades.
Sag Harbor also has a deep history as an inclusive, culturally welcoming haven. From the early 1800s, the Eastville section of Sag Harbor was home to a diverse community of free Blacks, European immigrants, and Native Americans. Sag Harbor continues to be a vital community for Black families, attracting artists, entrepreneurs and professionals.
Obviously, a lot to absorb and appreciate about Sag, but we were here one hot night with our panting dog. So instead, we made lists of places to check out on future trips:
· The Sag Harbor Whaling & Historical Museum
· The Bay Street Theater
Finding a Slip in Sag
Crossing the Long Island Sound from the Connecticut River, Sag Harbor is about as straightforward a navigation as going to Greenport. But it had always been on the “to visit” list, as we often stuck with the Greenport we knew. But one hot (very hot) summer weekend in July, we decided to break out of our comfort zone and go for it!
There are a handful of town docks and private yacht clubs, but for our easy overnight we reserved a slip with the Sag Harbor Village Marina. Coming from two nights in Mattituck, where the marina was tucked away down an inlet in a country-club setting, this was an entirely different feel. The approach, ease of reservations and attentiveness of dockhands were all positive and welcoming. But here in Sag Harbor, you step off your boat, walk up the docks and you are at the heart of Sag Harbor at the foot of bustling Main Street.
Coming from the west in Sag Harbor Bay, follow the channel until you to the Breakwater. You will see the marina on the port side. Hail the Sag Harbor Village Marina on UHF channel 09. The marina advises the bridge clearance is 17.5 feet at high tide and 20 feet at low tide, and the channel is 10 feet deep.
So if you’re coming from a place like Strong’s in Mattituck, with its spa-like facilities, it’s definitely a change of pace at this marina. The restrooms and showers are located about a 5 minute walk from the docks, in a building that’s part public facility, part marina guests. There are no frills to speak of… but then again you are staying at the center of the village, so.
You can reserve the Sag Harbor Village Marina on Dockwa.
Restaurants
The afternoon we arrived was a HOT one, and cold beers called to us. We had Ozzy with us, so we were thrilled to find The Corner Bar steps from the dock at the corner of Main Street and Bay streets , with several lattice-enclosed outdoor tables – and Blue Point Toasted Head on draft. Ozzy gave it two paws up! We loved it too.
After an afternoon of exploring, shopping, and ducking into our boat for some A/C, we opted for dinner at one of the few pet-friendly restaurants. It was no sacrifice to enjoy the sidewalk seating at the upscale Page on Main Street.
Our server was fun and attentive, the food was fresh and inspired, and Ozzy patiently perched under the table watching passersby. (I was a little less restrained when actor Victor Garber, who I loved in Godspell, strolled by.)
Info & Events
Find local events in Sag Harbor, including the Sag Harbor American Music Festival, September 26-28, 2025.
