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.
Open in the winter; nice, casual atmosphere. Raw bar + standard bar fare. Burgers and fish sandwich looked good.
Crowded but not too crazy in the winter; go fo the pancakes or stuffed crepes.
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.
At the tip of Montauk; pebbly beach walking and exploring with views of the lighthouse.
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.
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.
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.
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.
