Weekend Trip Idea: Montauk NY

I feel like it’s been a trend in all the travel blogs and magazines to feature summer-centric beach towns as fall destinations.  Since I’d like to be on trend, I’m going to follow suit.

They’ve been pointing out that after Labor Day the crowds abruptly disappear but since the weather hasn’t made the full fall transition yet, the ocean is still warm.  This isn’t the kind of getaway you’ll be wanting to take if you want a hopping, party filled destination but on the other hand you won’t be competing with the crowds for beach space, restaurant seating or room at the bar, plus you may get to see a more “authentic” side of the town and mingle with more locals then you would during the high tourist season.

My pick for an off season beach weekend would be Montauk, New York.  Montauk is located on the very end of Long Island, only 20 miles from the Connecticut coast and since you’ll have to travel the whole of Long Island, it’s a bit of a hike (I’d suggest a three day weekend or early Friday morning leave-time). There are plenty of more convenient off season beach locations (Rehoboth Beach for camping and beer tasting wouldn’t be a bad pick) but I’ve always wanted to visit Montauk and it seems to have a bit more year-round character then, for example, a lot of the Jersey shore towns during the off-season.

Montauk is considered the Hamptons but draws less of a blue-blooded, jet set crowd and is actually known as one of the better surfing spots in the Northeast, so if you’ve never gone before, why not try your hand at some lessons? My surfer friend Eric (who’s also frequently dragged on various outings with me and I believe is my most mentioned friend on this blog) tells me that some of the best surfing actually occurs in the fall & winter.

Montauk also has six state parks if you’re up for some hiking in the New English fall foliage (is Long Island New English?) and plenty of kayaking and paddleboarding opportunities as well. There’s a ton of companies to chose from but the one I’d look into is Weekend Warriors, in nearby Sag Harbor. Not only do they offer rentals, but guided tours, lessons, happy hour paddles and clambakes.

Montauk’s a huge fishing destination and in fact holds shark fishing tournaments, including one that was founded for the guy who was alleged to be the inspiration for Captain Quinn in Jaws.  If that thought leaves you uneasy and you think you’re going to need a bigger boat (see what I did there?), try the Mon Tiki, Montauk’s charter catamaran.

If the Jaws reference scared you so much you want to stay on shore, Montauk randomly has the oldest working dude ranch in the country.

I’m not usually one to get over excited about lodging (I feel like the last few trips I’ve taken were spent on floors or couches) Montauk has some cool options.  The Surf Lodge and Ruschmeyers are both throwbacks to a bygone surfing era (Ruschmeyer rooms come with hammocks) and The Memory Motel is listed on Tripadvisor as “cheap and creepy” (aka I’d probably love it) and is famous as the inspiration for the Rolling Stones song of the same name and a rowdy dive bar (aka I’d definitely be in love).