Gush all you want about summer, but locals and honorary locals alike will tell you the off-season is where it’s at. When the crowds head west and the roads turn sane and there are no longer the proverbial 10 pounds of bricks in a five-pound bag, that’s the time to emerge from reverse hibernation and hit the restaurants, the wineries, the trails.
It’s when you find a bench upstreet, a stool at a favorite watering hole, a table at the best restaurants (and when service is arguably at its peak). This is a guide for the seasonally agoraphobic, those who want to be alone, together with their favorite people. This world is your oyster! (And speaking of oysters, there’s a suggestion on that, too.)
Here, a list of ideas and a mini itinerary or two from someone who gets where you’re coming from.
Montauk Mini-Adventure
A dearly departed East Hampton Star writer used to call Montauk “God’s Country,” and it’s hard to disagree. For the crowd-averse, Montauk is even more of a paradise from November through May (and definitely put one of the below suggestions on your agenda for a September or October day next year). There could be dozens of variations on the perfect Montauk itinerary. Here, both involve the great outdoors and both end with refreshments.
First, a hike around Big Reed Pond, way out past the downtown, off East Lake Drive. Loops of different lengths allow you to choose the adventure you want: 3.8 miles, maybe as long as 4.5 miles, or a shorter in-and-back. The terrain has some very gentle hills, and the trails pass over streams on wooden footbridges, hug the pond, and could even include a section on the beach along the Block Island Sound. The plus of a cold-weather hike: fewer ticks.
Nearby, there’s another hike that requires some planning and some stamina but will get you so far from the “civilized” South Fork that you’ll feel like a contestant on a survival show. For this one, you’ll need two vehicles, because you’ll start at one spot and end at another. Go with a friend, or seven. It won’t disappoint. Leave one vehicle or more at the Gin Beach parking lot at the end of East Lake Drive (no permit required this time of year), collect fellow hikers there in another vehicle, and drive to Montauk Point, where there may be a parking fee depending on the month.
From there, head down to the water and walk along the north shore, picking your way over the stony coastline of Block Island Sound, passing the terminus of the Seal Haul-Out Trail, and continuing onward until you get to a spot where a dune separates the beach from Oyster Pond and eventually, a thin strip of sand from which you can peer in to the remote pond. Looking at a map, you might wonder if there’s an inlet here that’s impassable at high tide. There’s not, and on the other side of that strip, the walk becomes largely sandy: white sand, pink sand, black sand, barely marred by another footprint or tire track. Follow this peaceful, wildly beautiful windswept stretch all the way to the more frequently used Gin Beach. This one is 5.1 miles on stones and sand. It’s a challenge, so when you’re finished, celebrate.
In either case, the obvious next stop is Inlet Seafood, also at the end of East Lake Drive, open almost all fall and winter and with just about the best west-facing view anywhere. It’s owned by fishing families whose fresh catch makes up the bulk of the menu. Go for lunch after a morning hike or plan the walking to coincide with a sunset cocktail and dinner. The bar is four deep in the warmer months; savor the access of fall, winter, and spring, when the fish is as fresh as ever and there are frequent deals.
Also on the greatest hits list of Montauk walks: Amsterdam Beach, Point Woods Trail, the Seal Haul-Out Trail, and Shadmoor State Park, to name only a few. You could literally walk for days in Montauk.
Cap any of them with stops at the Montauk Brewing Co. for beers and spiked seltzers inside and outside in every season during the day, and takeout from the neighboring Street Food, maybe a table at the Shagwong Tavern, open all year on Main Street, or lunch at the healthier Naturally Good across the street.
If crowds aren’t your thing, the popular Montauket may be daunting in July, but in November you still get world-class, heart-stopping sunsets over Fort Pond Bay with easier parking and fewer people. It’s such a good way to end the day, you might not even need the walk first. If you’re coming from points even a little west and still think Montauk’s downtown is a ghost town in the off-season, you’ll be surprised at how much is open. Another year-round favorite for food with a sunset side is the Harvest on Fort Pond.
Sagaponack Grapes (and Grains)
Beautiful at any time of year, the tasting room in the Tuscan-style Wolffer Estate Vineyard winery building is magical and romantic as all get-out on a late fall or winter evening, and the inside ambience matches the outside vibe. Step through the heavy wooden front doors and you’ll feel instantly transported. This could be a hundreds-of-years-old winery in the French countryside, but there’s no plane ticket required.
The tasting room is open seven days a week. Walk-ins and last-minute “planners” are more likely to have success at this time of year. However, reservations can be made up to 14 days in advance for a 90-minute visit, during which you can sample from Wolffer’s reds, whites, rosés, ciders, spirits, seasonal cocktails, and even nonalcoholic offerings, and order from a menu that includes light bites, charcuterie boards, cheese plates, and warm flatbreads. In late fall and winter, the weekly Candlelight Friday series adds music to the mix from 4 to 7 p.m. Guided tours, accompanied by a sommelier, include cheese and charcuterie. Last winter, the winery ran a Ladies Night on Thursdays starting in February.
Just down Sagg Road, but for a different day — no mixing — the Sagaponack Farm Distillery has a tasting room of its own, also open all winter. Spirits created by the Foster family utilizing ingredients grown on the family farm — vodka, gin, bourbon, rye, and a “single spud” akin to whiskey — are the stars of the cocktail menu here, and on select weekends, food trucks are on hand too.
Shop (and Eat) Sag Harbor
The throngs that flock to Sag Harbor in July or August — there’s so much to eat, drink, buy, and ogle — might be a turnoff if you’re just trying to get a cup of coffee or pick something up at the hardware store. Forty-five minutes to drive the less than 10 miles between East Hampton and Sag Harbor? No thanks. If you feel like your visits to this vibrant downtown in the summertime are “confined to the margins of the day,” to quote The Star’s Christopher Gangemi, well, there’s a spot on a Main Street bench for you right now.
Wade in slowly, from the edges. Do breakfast at Harbor Market, on the corner of Henry and Division Streets, with the option to eat at one of the few tables or take it to go. Coffee is a personal thing, and each of the many java joints have their devotees: Grindstone Coffee and Donuts, Jack’s Stir Brew, Sagtown Coffee, Sylvester and Co. Modern General. If tea’s your bag, the best house-made chai this side of anywhere can be had at Provisions, the natural food market on the corner of Bay and Division Streets.
Then do what you might not do all summer. Go shopping on Main Street, where there are still plenty of boutiques you won’t find in SoHo, East Hampton Village, or on Rodeo Drive (and a few you might), along with a fabulous hardware store, the famously useful Sag Harbor Variety Store, and a really super I.G.A., Schiavoni’s Market.
Grab lunch, squeeze in an afternoon matinee at the impressive Sag Harbor Cinema, and cap that with a stop at the tasting room of the Kidd Squid Brewing Company on Spring Street. It serves its own beers and has seating inside and outside as weather allows, and live music on select evenings. It’s not open late; if you try to go after dinner, you may be disappointed. And speaking of dinner (or breakfast or lunch), the American Hotel gets the nod for the most iconic of the village’s many great restaurants, Plus, The Star’s fishing columnist, Jon M. Diat, swears it has the best Tuesday night deal on the best oysters. Don’t be shy, get gussied up and treat yourself.
