The Hamptons are at their quaintest during the holiday season, when the summer crowds have thinned, the villages are adorned with wreaths and ribbons, and locals’ calendars are filled with festive gatherings.
December begins with the annual Christmas Bazaar and Tea at the Westhampton Presbyterian Church on the first of the month. After an elegant Silver Tea, start checking off names on your gift list as you peruse the handmade ornaments, wreaths, and jewelry. Stick around for the Westhampton Beach Christmas Tree and Menorah Lighting on the Village Green at 5:30pm. Feast on latkes and cookies while you enjoy the sounds of carolers and a local youth choir.
On December 8, WinterFest storms through town from 11am to 3pm, with horse and buggy rides along Main Street, crafts, story time and photos with Santa. Warm up around the fireplace in the decorated-to-the-nines Beach Bakery Café, serving homemade pastries and Dutch hot chocolate. Don’t leave without one of the adorable and delicious gingerbread houses.
The Westhampton Beach Performing Arts Center is home to seasonal entertainment as well. The Vienna Boys Choir will take the stage on December 9 at 7:30pm with a repertoire that includes peppy pop songs and moving holiday pieces like “Stille Nacht” (“Silent Night”). Local children will perform alongside professional ballet dancers in two performances of The Nutcracker on December 15 at 7pm and December 16 at 3pm.
Family friendly dinner options include Baby Moon Restaurant for Italian food, where the calamari and chicken parm are sure to please. Seafood lovers can snag a table near the fireplace at Buoy One. Order the fisherman’s basket if you want to sample fried filet, shrimp, scallops, clams and sides. No room for dessert? Keep it seasonal with gingerbread Kahlua coffee.
When you’re ready to hit the shops without trudging through the mall, head to Main Street. Mustique has faux fur boot cuffs for women and cozy velour hooded bathrobes or embroidered flasks for the men on your list. Little Red Wagon has wares for all the tykes, whether you want high-end baby clothes or puzzles and puppets. Main Street Sweets has oversize Pez dispensers—the perfect stocking stuffer for any age.
Youngsters can make their own gifts at Studio Art; the array of classes includes fashion design, batik, making signature perfumes and mixing bubble bath.
Southampton residents are busy on December 1, when the town officially ushers in the holiday season with the “It’s a Wonderful Village” Holiday Stroll, complete with horse and buggy rides, carolers, and the Agawam Park Tree Lighting. The Southampton Cultural Center also opens its doors to the public at 5:30pm for their annual holiday party. A visit from Saint Nick, refreshments and live music complete the evening.
The Greek revival style Rogers Mansion, built in 1843, will host many holiday festivities, including an ongoing exhibit (November 10 to January 5) entitled 1950s Christmas in Southampton. Visitors can learn about toys, gifts, and decorations from that era and even visit a recreated 1950s living room. The mansion, which is part of the Southampton Historical Museum, will host Hearthside Cheer on December 1 from 5:30-7:30pm. Plans include open bar, hors d-oeuvres, live pianists and antique decorations throughout the parlors, sitting rooms and reception rooms. Tickets are $50 for non-members and can be purchased by calling (631) 283-2494.
Ardent bakers can return to the mansion on December 12 at 4pm for the Annual Cookie Exchange. Expect to sample lots of yummy concoctions and receive dozens of recipes. Cost is $5 per person.
Escape the hustle and bustle and join a naturalist from SoFo, the South Fork Natural History Museum and Nature Center, on a Family Forest Walk on December 1. Together you will explore the forest in transition between seasons, far form the bustling shops and crowded calendars that come with the holidays. Call (631) 537-9735 to reserve spots ($7 adults and $5 children).
Shinnecock Nation Cultural Center and Museum will host their Winter Festival on December 8 from 11am to 4pm. Native American artists will demonstrate wampum bead making, open fire cooking and authentic dances. Interpreters in 17th century Shinnecock clothing will be on hand to lead guests through the artisan market, where vendors will sell jewelry, ceramics and wood carvings. Food options include succotash soup and locally cultivated oysters.
For authentic Sicilian food made with locally grown and caught ingredients, try Osteria Salina. Top off the grilled swordfish with flourless chocolate cake.
Or try the fresh sushi and sashimi in a quaint cottage setting at Yama-Q.
For one-stop shopping, head to Hildreth’s, the oldest department store in the US. Grab lotions, linens, candles, children’s clothing, home furnishings—this Main Street staple has something for everyone on your gift list.
Learn how to make your own unique Christmas wreath at a hands-on workshop at Bridge Gardens on December 2 from 2 to 4pm. Register by calling (631) 283-3195 ($30 per person), and bring work gloves, shears and any decorative items, like seashells or lights.
On December 17, kids can join SoFo educators as they use seeds, dried fruit, and suet to make bird-friendly holiday ornaments for your outdoor trees ($2 per child).
Escape the chaos between Christmas and New Year’s Eve with a Full Snow Moon Hike alongside members of Friends of the Long Pond Greenbelt. The leisurely stroll on December 28 at 6:30pm will be followed by refreshments.
Channing Daughters Winery, one of the South Fork’s smaller vineyards, offers a taste of six wines for $10, but reserve ahead for groups of seven or more.
Tutto Bene, which means “everything good” in Italian, is a must for Main Street shoppers. The women’s boutique has clothes and accessories for every taste and budget, and hot stocking stuffers this year are texting gloves, so you can stay on top of your social networking without getting cold fingers. They come in a variety of colors and cost just $28. Continue browsing at Maison 24, home of the trendiest menswear and home goods.
The old-fashioned Candy Kitchen Ice Cream Parlour and Eatery is perfect for a laid-back atmosphere. The menu is that of a typical diner (think omelettes and turkey clubs) but the ice cream sodas are phenomenal. For a more upscale setting, Almond is a French bistro with a variety of steaks and great bread. The wine list includes local whites.
The Santa Parade will roll along Main Street on December 1, complete with floats, antique cars and throngs of local kids donning Santa hats, before the big guy himself (and his Mrs. of course) arrives at the end. St. Nick returns to town on December 8 for the annual Holiday Stroll, where he lights the trees in Pulaski Park from atop a fire truck, then poses for photo ops in the decorated bandstand. Christmas carols, hot chocolate and cookies will finish off the festive evening.
If you can’t afford a weekend of upscale accommodations, book a spot on the 12/8 Holiday Tour of Inns, B & Bs, and Special Places. You’ll visit historic landmarks to put on your wish list for next summer’s accommodations. On 12/9, visit The Maidstone at c/o the Living Room for the annual tree lighting. Bring food and toy donations and enjoy cookie decorating, pictures with Santa, holiday music, and raffles.
Lace up a pair of skates and hit the ice rink at Buckskill Winter Club ($23 per adult on weekends, $7 skate rentals). When your toes get numb, head into the clubhouse and warm up by the fire with a hot chocolate.
Main Street is home to a medley of shops, from Tiffany & Co. to antiques stores and art galleries. Home, James! is perfect if you’re looking for new linens, china and crystal to host a holiday gathering. BookHampton has a large selection of coffee table books and children’s classics.
Make Nick & Toni’s, the summer place-to-be-seen, your dinner spot now that the crowds have headed back to the city. The menu, which changes seasonally, is filled with locally grown products. Or head to The Palm, inside the 300-year-old building that is also home to The Huntting Inn. Warm up with lobster bisque followed by your choice of six cuts of steak and delectable flourless chocolate cake.
The quaint town of Sag Harbor will host the annual Holiday Light Up and Tree Lighting on December 1, featuring Santa and old-fashioned holiday cheer. Taste the wines from Wölffer Estate Vineyard, or shop at Flashbacks for women’s fashions and accessories with an Indonesian flair. Wares at the Wharf Shop include dollhouses and Native American jewelry.