A Perfect Day: Post-Seasoner

There may be no better month in Montauk than October.* Coming out for a wedding (no shortage of them this time of year), hankering for a walk on an empty stretch of sand or looking to eyeball the gorgeous palette of trees (closer to the end of the month), you’ll find there’s no wrong way to do this. But just to make sure...


9 AM

John’s Pancake House, a longstanding local spot with no-nonsense waitresses, opens its doors at 6 a.m. and closes them at 3 p.m. Get there as early as you can to dig into the pancakes—we’d go with the banana nut—eggs, coffee, the usual old-school diner stuff. Perfect carb-loading to get you through the morning’s fun.

John’s Pancake House
721 Main St., just a few doors down from our Montauk Mainstay store. (631) 668-2382


11 AM

You can go a few ways on burning off some of those carbs—on horseback, on foot or a combo of both.

If you opt for the equine, call in advance for a crazy-scenic trail/beach ride at Deep Hollow Ranch (which claims to be the oldest working ranch in the US); rides range from 30 mins to 1-1/2 hours and can include a trot through Montauk Point State park along Block Island Sound.

Deep Hollow Ranch
1929 Montauk Hwy. (631) 668-2744


11 or 12:30 PM

If you prefer keeping your feet on the ground or want to work out some kinks post-ride, the Amsterdam Beach trail is right across Rt. 27 from the ranch. It wends through woods out to the Atlantic, with windswept views of the dunes, ocean and the former Warhol estate. You can also drive out a little further east to Camp Hero, former Army and Air Force bases. Expect jaw to meet ground when you see the vista but don’t treat the “danger” signs near the cliff edges lightly; those bluffs are seriously undercut. Set off through the woodsy eastern trail to get down to the rocky beach at the foot of the lighthouse. Unless you’ve got to see the spooky abandoned radar tower up close; then head west.

Amsterdam Beach Preserve
Rt. 27, parking lot (free), across from DHR

Camp Hero
Rt. 27 just west of Montauk Lighthouse ($8 parking fee), (631) 668-3781



You deserve some seriously tasty pub food, Montauk style. The Dock is down at the marina, filled with a mix of locals and visitors, and the perfect fall-day spot. Word to the wise once you set foot in here: Do not attempt to use your cell phone. Do not throw George, the owner who’s often behind the bar, even half an ounce of attitude. Now, enjoy.

The Dock
482 West Lake Dr. (631) 668-9778


3:30 PM

You could go catch some zzzzs. Or you could decide it’s time for wine. The prettiest/most autumn-y place to taste is Wölffer. And the wine’s pretty fine too. (You may’ve drunk your share of Wölffer rosé this summer.) The rustic-chic tasting room opens to a stone terrace; there’s also a wine bar that does the reclaimed wood/banquettes thing very well. Remember, the key here is tasting.

Wölffer Estate Vineyards
139 Sagg Road, Sagaponack, about 35 mins west of Montauk (631) 537-5106


7:30-ish PM

We’re feeling Harvest, which sits on Fort Pond. It’s the perfect kind of place to eat at the bar, or if you’re a bigger group and rez-less, it’ll be faster to get a table outside in the colorful garden, where heat lamps keep things cozy. Portions are family-style so “sharing” is the word of the night. And, the special list of $20 bottles of wine, none bad.

Harvest on Fort Pond
11 S. Emery St (631) 668-5574


*If you’re heading out the weekend of Oct. 8, the annual Chowder festival will be happening on the town green. It starts on Sat. at 11 am and if you want chowder, you need to be there then. It’s gone within the hour.



Photography by:
Mark Weinberg