Yes, You Can Afford The Hamptons — Here's The Trick

As much fun as it is prepping our fall wardrobe (leather skirts! Topcoats! Lace-up booties!), we can't help but daydream about summer. The lobster rolls, the ocean breeze, the sweet smell of sunscreen — okay, we miss the beach a little too much.
Have you ever wondered, though, why places like the Hamptons empty out as soon as Labor Day comes? The beaches are still there, the weather is even more pleasant (goodbye humidity!), and a plethora of restaurants and hotels are still open. Plus, since most people don't think of the Hamptons as anything more than a summer destination, the towns are so much more relaxed in the off-season. It's easier to make reservations, hotel rates are lower, crowds everywhere are thinner, and there are some awesome events that happen in the months that follow.
And, while it pains us to reveal our secrets for taking on the Hamptons in the fall, we just couldn't keep them to ourselves. Meet you in Montauk!
1 of 10
Photo: Courtesy of Montauk Blue.
Montauk Blue Hotel

The crowds have thinned and the leaves are beginning to turn, which means that October is probably the most peaceful time of year in the Hamptons. And, luckily, one of our favorite Montauk hotels is open until November (and offers a complimentary tasting at the Montauk Brewing Company with a two-night stay). The Montauk Blue Hotel has oceanfront rooms — all with decks — direct access to the beach, and an indoor pool and hot tub. It's the ideal spot for a cool-weather visit, since it doesn't need to be warm out for you to enjoy the beauty, sound, and breeze of the beach.

Montauk Blue Hotel, 108 South Emerson Avenue (between South Edgemere and South Embassy streets), Montauk; 631-668-4000.
2 of 10
Photo: Courtesy of Bell & Anchor.
The Bell & Anchor

If you want to eat locally, look no further than The Bell & Anchor. Serving the best seafood, steak, and beer on the Atlantic, this Sag Harbor waterside restaurant has become a hot spot for Hampton-dwellers over the years. Slurp away on delicious Montauk Pearls (served year-round for $1.50 a pop) as you watch the boats sail away.

The Bell & Anchor, 3253 Noyac Road, Sag Harbor; 631-725-3400.
3 of 10
Photo: Courtesy of Hamptons International Film Festival.
Hamptons International Film Festival

Think Hollywood only hits the Hamptons come summer? Think again. Every October, movie industry folk gather near the shore to celebrate the best in independent films. Plan your visit during this time of year to catch a flick, spot some celebs, or simply enjoy the other area events that coincide with the fest.

Hamptons International Film Festival, Various Cinemas, October 9 to 13.
4 of 10
Photo: Courtesy of ℅ Maidstone.
℅ The Maidstone

This eclectic East Hampton hotel prides itself on being extra cozy, which means it's basically meant for cold weather. Designed with the intention of making everyone feel at home, the Scandinavian-inspired interior boasts an array of bold colors and sleek accessories. In the off-season (which is significantly cheaper, especially if you book during the week), snuggle up in front of one of its many fireplaces with a good book, or kick back and relax at afternoon tea in the aptly named "Cozy Lounge." Yeah, you'll probably never want to leave.

℅ The Maidstone, 207 Main Street (at Maiden Hill Lane), East Hampton; 631-324-5006.
5 of 10
Photo: Courtesy of Sag Harbor Sailing.
Fishing Excursions

You may not consider yourself a grade-A fisherman, but there's no reason you shouldn't experience the famed Hamptons Fall Blitz (the time of the year when Striped Bass, False Albacore, and Bluefish gather around the East End in droves before migrating south). Thanks to the fish migration patterns, September through November has become the perfect time to do some fishing. Hop on a boat excursion with Sag Harbor Sailing for a few hours of fly fishing, or take part in some of Viking Fleet's themed events, like the Special Full Moon Moo Cow Madness and Sunrise Live Eel Trips.

Sag Harbor Sailing, 51 Pineneck Avenue, Sag Harbor; 631-725-5100; Viking Fleet, 462 West Lake Drive, Montauk; 631-668-5700.
6 of 10
Photo: Courtesy of Rowdy Hall.
Rowdy Hall

Rowdy Hall is the place you go to for warmth — and we're not just talking about finding respite from the cold. The atmosphere and people at this East Hampton landmark are so warm and friendly, you’ll feel like a regular after your first visit. Its classic pub fare menu is packed to the brim with hearty comfort food — fish and chips, Black Angus burgers, French onion soup — which is basically everything we could ask for when those temperatures drop. Oh, and they throw a mean Halloween party, in case you're looking to head east for some trick-or-treating.

Rowdy Hall, 10 Main Street, East Hampton; 631-324-8555.
7 of 10
Photo: Courtesy of Wölffer Estate Winery.
Wine Tasting

Remember that delicious wine you had with dinner last summer in the Hamptons? Believe it or not, it was made right down the road. Long Island is a hidden gem when it comes to wineries, and we highly recommend a tour and tasting at the local vineyards. Plus, the best time to visit wineries, like Wölffer Estate (where $10 Wölffer Wednesdays range from vineyard walks to poetry nights) and Channing Daughters, is in the fall, during harvesting. See grapes at their fullest and experience the vineyards at their prime. By next summer, you’ll be an expert.

Wölffer Estate, 139 Sagg Road, Sagaponack; 631-537-5106; Channing Daughters, 1927 Scuttle Hole Road, Bridgehampton; 631-537-7224.
8 of 10
Photo: Courtesy of Topping Rose House.
Topping Rose House

Topping Rose House is the place for maintaining the luxury and trendiness of the Hamptons, even when summer is long gone. Open year-round, this idyllic destination is located in close proximity to the best non-beach activities Bridgehampton has to offer, from boutiques and restaurants to art galleries. Take advantage of the property's gorgeous pool (for those warmer fall days), rejuvenating spa, and farm-to-table eatery (operated by Tom Colicchio), with one of its winter packages. (One includes a spa weekend; another features an array of fine dining options.) It's the ultimate oasis, and only 100 miles from New York City.

Topping Rose House, 1 Bridgehampton-Sag Harbor Turnpike (at Ocean Road), Bridgehampton; 631-537-0870.
9 of 10
Photo: Courtesy of Swallow East.
Swallow East

The running joke in Montauk may be that the town's gates literally close come Labor Day, but Swallow East proves otherwise. Swallow's enclosed deck offers waterfront dining year-round, and its lively atmosphere promises the spirit of the Hamptons, regardless of the weather. Bring your friends for a fun night of shared plates (blue claw crab croquettes, asparagus fries, local chowder) and bottled cocktails; Tuesday through Friday, get 50% off drinks and all menu items at the bar from 5 to 6:30 p.m.

Swallow East, 474 West Lake Drive, Montauk; 631-668-8344.
10 of 10
Photo: Courtesy of Southampton Publick House.
Southampton Publick House

For the most authentic East End experience, top off your evening with a visit to this Southampton hot spot. Known for its award-winning beers (many of which are brewed on-site), Publick House also has a variety of happy hours and DJ lineups for a fun night out. Plus, with Oktoberfest just around the corner and fresh pumpkin ale on tap, this microbrewery is a cool hangout for any crisp autumn evening.

Southampton Publick House, 40 Bowden Square (at North Sea Road), Southampton; 631-283-2800.