Easthampton is a very pretty village. for unusual i would suggest Home Sweet Home Museum http://homesweethomemuseum.org/index.html but they are closed in the winter. there are three windmills you could take a peek at: Hook Mill, Pantigo Mill and Gardiner Mill. a few were from England, but many of the first settlers came from Lynn Massachusetts in the 1600s. winter in the Hamptons is a bit low-key but you will find restaurants open. some of the dinner eateries change hands so frequently and many close for the winter.
traffic can be heavy at times (driving west due to the low level of the sun) especially between 3:00 and 6:00 pm there is just one main road from Southampton on to points east. there is a ton of service business year round. someone needs to keep the heating and plumbing going in the mansions!
this is the local news website with a Dining sections which may help:
http://www.27east.com/food/town.cfm/East%20Hampton
Quick bites
The Golden Pear is a longtime establishment and is a cafe for breakfast/lunch and has locations in Easthampton, Southampton and Bridgehampton and Sag Harbor.
http://www.goldenpearcafe.com/
Silvers in Southampton has been there forever - another quick bites if you are out and about in Southampton.
http://silversrestaurant.com/
Wine
Duck Walk Vineyards in Water Mill has some events in Feb. Water Mill is about 10 minutes drive east from Southampton and will be about 20-25 minutes west of Easthampton.
North Shore Vineyards:
you can travel to Sag Harbor from Easthampton, take the Shelter Island Ferry to Greenport. Greenport is a cute village. you can make your way to the wineries from Greenport (use a GPS - they are easy to find without one though)
Martha Clara on the North Shore - they do a lot of live music summer and winter and wine pairings. i really like their wine and they have generous pours.
www.marthaclaravineyards.com
Pindar Vineyards have winepairings: Pindar has been around forever
www.pindar.net
Castello di Borghese is the original Hargraves vineyard. The Hargraves were the first to come to LI to plant grapes in the early 70s. http://castellodiborghese.com
the North Shore is even quieter than the Hamptons in the winter
Back to the Easthampton Area...check out the ocean, and Montauk Lighthouse is a nice ride. there is a shore route off 27a that takes you along the ocean - don't miss it is a gorgeous drive, especially so if there are nice long barrell waves. 9 out of 10 you will see many surfers out there. Lobster Roll is closed for the season but there may be a restaurant open in Montauk.
enjoy your holiday out there! very casual, warm sweaters and cozy boots!
Edit to add: Sag Harbor is fun too - they have events going on as they are a bit more artsy and earthy crunchy in a Hamptons way. Sag Harbor was a Whaling Port and i think there is a museum.
if you need a Mall shopping fix there are Tanger Outlets in Riverhead. will be an hour drive there :-( but there are 2 outlet complexes with all the usual suspects :-)
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