Montauk! Winter edition!
The Walking Dune Trail is one of Montauk! Winter edition!.

1. The Walking Dune Trail

7.4
Napeague Harbor Rd, Montauk, NY
Trail · 4 tips and reviews

Talisa C.Talisa Chang: A pleasant & super pretty 3/4 mile walk (give yourself a leisurely hour) through giant sand dunes that spits you out on the Napeague beach. (Also for walking, not swimming). Perfect quiet winter walk.

Shagwong Restaurant is one of Montauk! Winter edition!.

2. Shagwong Restaurant

7.1
774 Main St, Montauk, NY
Pub · 33 tips and reviews

Talisa C.Talisa Chang: Open in the winter; nice, casual atmosphere. Raw bar + standard bar fare. Burgers and fish sandwich looked good.

Mr. John's Pancake House is one of Montauk! Winter edition!.

3. Mr. John's Pancake House

7.2
721 Main St (The Plaza), Montauk, NY
Diner · 49 tips and reviews

Talisa C.Talisa Chang: Crowded but not too crazy in the winter; go fo the pancakes or stuffed crepes.

Ditch Plains Beach is one of Montauk! Winter edition!.

4. Ditch Plains Beach

9.3
Montauk Hwy, Montauk, NY
Surf Spot · 32 tips and reviews

Talisa C.Talisa Chang: Swim/surf beach; super quiet in the winter - don't expect the food spots to be open. Stroll or bike around the nabe and plot your summer rental dreams.

Montauk Point State Park is one of Montauk! Winter edition!.

5. Montauk Point State Park

8.6
2000 Montauk Hwy, Montauk, NY
Park · 9 tips and reviews

Talisa C.Talisa Chang: At the tip of Montauk; pebbly beach walking and exploring with views of the lighthouse.

The Milk Pail is one of Montauk! Winter edition!.

6. The Milk Pail

7.4
1346 Montauk Hwy, Watermill, NY
Farmers Market · 3 tips and reviews

Michael T.Michael Thiele: This location is back to being open year-round. The apple cider donuts are amazing - try to get them right out of the fryer. Excellent cider, pies and applesauce that they make themselves.

Montauk Manor is one of Montauk! Winter edition!.

7. Montauk Manor

8.0
236 Edgemere St, Montauk, NY
Hotel · 14 tips and reviews

Talisa C.Talisa Chang: Renovated murder mystery looking mansion with manageable off-season rates. Indoor pool / hot tub and complimentary breakfast. Our duplex came with a kitchen and living room setup.

East By Northeast is one of Montauk! Winter edition!.

8. East By Northeast

7.8
51 Edgemere St, Montauk, NY
Asian Restaurant · 24 tips and reviews

Talisa C.Talisa Chang: Hit or miss fusion-y food with a lovely lake / sunset view. Off-season $15 prix fixe dinner before 7pm (Sun-Thurs) is a steal. Stick to ordering things that make culinary sense.

Montauket is one of Montauk! Winter edition!.

9. Montauket

8.9
88 Firestone Rd, Montauk, NY
Seafood Restaurant · 29 tips and reviews

Talisa C.Talisa Chang: Super quiet in the winter, but open! Relax and watch the water at the bar.

Navy Road Beach is one of Montauk! Winter edition!.

10. Navy Road Beach

6.6
Navy Rd (Shore Rd), Montauk, NY
Beach · 6 tips and reviews

Talisa C.Talisa Chang: Finds: shot gun pellets, empty wine bottles. Not for swimming.

Montauk Beach is one of Montauk! Winter edition!.

11. Montauk Beach

9.1
Ocean (at S Edgemere St), Montauk, NY
Beach · Montauk · 37 tips and reviews

Talisa C.Talisa Chang: Your standard sandy, swimmy beach.

John's Drive-In is one of Montauk! Winter edition!.

12. John's Drive-In

8.1
677 Montauk Hwy, Montauk, NY
Ice Cream Shop · 51 tips and reviews

Talisa C.Talisa Chang: Burgers, shakes, fries, fish n chips. Open in the winter but limited hours.

Oyster Pond is one of Montauk! Winter edition!.

13. Oyster Pond

Drainage to (Block Island Sound), Montauk, NY
Lake · 1 tip

Talisa C.Talisa Chang: Peaceful and pretty pond/lake. Take the trail at Long Field road off the 27 (small parking inlet). Wide, vehicle wide trail will take you straight to the pond; lots of smaller trails to explore.

Napeague Harbor Beach is one of Montauk! Winter edition!.

14. Napeague Harbor Beach

Napeague Harbor Rd, Montauk, NY
Beach · 1 tip

Talisa C.Talisa Chang: Nice quiet, dog-walking beach. Near the Walking Dunes.

Indian Wells Tavern is one of Montauk! Winter edition!.

15. Indian Wells Tavern

8.0
Main Street, Amagansett, NY
Bar · 29 tips and reviews