“I’m going on a picnic and I’m going to bring an appetite, brewery hit list, cash and a designated driver.” Okay, so this isn’t exactly a picnic and it’s not really a road trip either. Think of it as an East End food and brewery tour minus the Hamptons traffic. Instead you’ll take a few shortcuts right across the water—with a little help from the ferry. The journey begins in Southampton.
Southampton Publick House is one of Long Island’s oldest breweries, but this year it made an unexpected move. After the building was sold, the brewery found a new, smaller home on Main Street. Though centrally located with ample in- and outdoor seating, it will likely be a temporary fix. The space constraints mean that, for now, all beer is being brewed off premise by head brewer Evan Addario. This has led to a more limited tap list but no drop off in quality. Though the town of Southampton obviously has more to offer, after enjoying a flight or pint at the brewery you’ll be taking a short drive to Sag Harbor to catch your first ferry.
Taking the ferry over to Shelter Island is a hassle-free affair. They come about every 15 minutes, there’s no need to make an advance reservation, and you can drive your car right on—but this is where you’ll need to dip into the cash we mentioned earlier. The trip itself is short yet scenic and before you know it you’re on the south side of Shelter Island.
By now, you should be pretty hungry. Even if you’re not, try to find some room because you’re not going to want to miss the Mexican food at Maria’s Kitchen. You were probably expecting a waterfront lobster roll or heaping dish of fried seafood for lunch, but just trust us. The inside of Maria’s is nothing more than a small deli with counter service, but there’s seating out back. Authentic street tacos on fresh-made corn tortillas, tortas and overstuffed burritos, featuring everything from beef tongue and pig’s ear to chorizo and chicken, adorn the menu. The fish taco is one of the best we’ve tried, and if you get there early enough, try the chilaquiles—think a twist on breakfast nachos that will keep you going all day.
Next door, Shelter Island Brewery is a family operation. Longtime resident Jim Hull opened the brewery over a year ago, and his daughter, Allison, can usually be found behind the tasting room bar. Typically there are six to eight beers on tap, many featuring locally harvested ingredients such as beach plums and lemon verbena. Due to the extremely small capacity of the brewery, beer can sometimes be low after a busy weekend. Flights are available and shareable, so you can sample all the beers then settle on a full pour.
Before you head out, take a little time to explore the island. It’s small so don’t worry too much about getting lost. Most beaches require a residency sticker to park your car, but the Mashomack Preserve is a great place to take a nature break and walk off the Mexican food and beer.
The ferry to Greenport leaves from the north side of the island and, again, no reservation is necessary; it’s quick and you can drive right on. Once docked in Greenport, you are basically in the heart of the town and it’s time to find parking and ditch the car for a while. The original Greenport Brewery still inhabits an old firehouse on Carpenter Street, though its operations have expanded to include a production facility and tasting room in Peconic. Fittingly, the original location is now brewing up an OG (original gravity or original gangster, depending on who you ask) series. These smaller, experimental batches have included a dry hopped sour, coffee stout and blueberry Berliner. The tasting room is a laid-back place to enjoy a pint, flight or both before checking out the rest of Greenport.
At the edge of town, but still well within walking distance, is Stirling Sake. Small Japanese plates and a limited sushi menu accompany a carefully curated seasonal sake menu. The staff is knowledgeable and will be happy to help you select the perfect sake. We usually opt to split a flight and an order of housemade pickles.
From there, head over to 1943 Pizza Bar for a more substantial dinner. Freshly made thin-crust pizzas are cooked to perfection in their brick oven. Toppings range from the usual meatballs, mushrooms and pepperoni to “curiously good” options like mashed potatoes and a fresh egg. Outdoor seating is available and a small tap list usually features a couple local beers (and wines), if you’re looking for something to wash your pizza down with.
Once again, you may want to walk around Greenport and enjoy the quaint, waterfront town before hopping back in your car for the double ferry ride back to Sag Harbor. If you’re anything like us, you’ll probably spend the trip home planning your next out east adventure.