Driving East towards Montauk what are the best tourist stops?Edited: 14 September 2016, 17:18
Depends on what you want to see/do, how much time you have and how many times you want to stop. There's the outlet mall in Riverhead. There's an Aquarium in Riverhead if you have kids with you. Pumpkintown in Watermill should be opening soon and is a huge draw for families with young kids ( and causes huge traffic snarls). The Hamptons villages are quite pretty, especially East Hampton.
Sag Harbor is slightly out of the way, but not much
My family lives in Sag Harbor and we do not celebrate Christmas so I can tell you first hand - the villages shut down for the day. It's small town USA out there and it's lovely so nobody is working on Xmas except for the movie theater, 7-11, the gas station and the one or two Chinese food places. Driving out for the day on Xmas would be a complete waste, I suggest that you stay in Manhattan where many things remain open and many people do not celebrate Christmas. In Manhattan it feels like a slow day in the big city, it's less busy but things are open and it's fun to walk around Rockefeller Center and Central/ Washington Square Park, the store windows - all of it. I can probably write a book about all the fun Christmas stuff to do in Manhattan from a person who doesn't celebrate the holiday.
While I agree there is much more open and happening in NYC on Xmas day, I wouldn't go so far as to call visiting the Hamptons a waste. If you're into shopping, yes, then it's a waste. But there are always at least 2 places open serving a xmas meal, Pierre's in Bridgehampton and the American Hotel in Sag Harbor. The beaches don't disappear. 👣 But since xmas falls on a Sunday this year, what I might do is plan at least one overnight so you get either Sat or Mon. when more things are open.
Off the top of my head I can list about 40-50 amazing fun interesting historical things to do in the Hamptons that will all be closed on Christmas and Pierre's is lovely (we go there for Thanksgiving) so if you want to drive 100 miles to eat dinner in a quaint village restaurant then come on out. However if you want to visit the many museums (childrens, historical and fine arts), visit the first customs house in The US visit a lighthouse, ride a ferry, tour historic homes and windmills, learn about the revolution, visiting sculpture parks and nature preserves, enjoy wine tastings and vineyard tours, attend live theater/ sand up comedy/ music or just see people walking around enjoying instead of deserted streets then take the drive out on a day that is not Christmas, in these small villages people stay home and celebrate, it will feel like a ghost town for someone without a family/ friends to visit.
Yes, but closed on Christmas - as is practically everything else.
The original OP asked about sites to stop at coming from Massapequa Park, Long Island NY.
That question was overtaken by a post from Brisbane, Australia about travelling on Christmas Day.
For the original question: Your drive should be less than 3 hours on a normal day.
What are you interested in? browsing boutiques.....perhaps stop in Westhampton, Southampton, Bridgehampton or East Hampton & take a look around. Will you have kids with you? Perhaps Pumpkintown in Watermill, as suggested. Like to see the Shinnecock Canal?
Without knowing your interests, the ages etc it's hard to tell you where to stop. I'd drive straight thru.
Why are people responding to an 11 month old question?