The holiday season is in full swing here on the East End. Our Main Streets are lined with colorfully lit trees, the stores are bustling with shoppers, and the social calendar is quickly filling up with parties and festivities. It’s no wonder locals cherish this time of year before old man winter howls into town and we hunker down for the colder months. For many, work schedules are a little bit less intense, it’s not too numbingly cold out there yet, and it’s a great time to catch up with friends and family while enjoying the beauty of our natural landscape and historic hamlets. Looking for some ideas to get into the Hamptons holiday groove? Here are some tips:

HOLIDAY SHOPPING | Spend an afternoon strolling and shopping in one of the East End’s beautiful coastal villages. A favorite must-stop in December is Sag Harbor. With its old-school charm and wide variety of interesting shops to poke around in, you can work on checking off your gift list and then take a break to refuel at a local eatery, like the festively decorated American Hotel or Baron’s Cove. Online shopping is fine, but it pales in comparison to the in-person shopping experience you’ll find in one of our hamlets—and, you’ll be doing a good deed by supporting our local merchants. It’s a win-win! Another great spot for holiday shopping is the markets that pop up in December. On the weekend of Dec. 16 – 17, there will be an Artist & Artisan Holiday Market sale at Ashawagh Hall in East Hampton, featuring all kinds of handmade gifts.

MUSIC & DANCE PERFORMANCES | From Christmas carols to ballet recitals—there’s a full roster of musical and theatrical performances happening this month around the East End to celebrate the holiday season. On my radar? The Wonderful Christmastime concert at the East Hampton Presbyterian Church on Dec. 15 (admission: non-perishable food pantry items and/or new adult-sized hoodies for Maureen’s Haven), and A Good Old Fashioned Holiday Cabaret on Dec. 16 at The Church in Sag Harbor. Check the local papers and online calendars for more happenings. It’s a great way to get into the spirit of the season and to support our local arts organizations (and a much-needed respite from all the shopping, partying, and eating!).

VISIT A LOCAL MUSEUM | This is the perfect time of year to visit a local museum or historic spot you’ve been meaning to check out before they take a winter break. The summer crowds are gone and many sites are decked out for the holidays and even offer special seasonal programming and events for the whole family. Over in Southampton at the Southampton History Museum, there’s a vintage  Holiday Toy Scavenger Hunt visitors can partake in through the end of the year, and at the Bridgehampton Museum, will host Gifts & Carols: A Community Singalong on Dec. 16, where participants are asked to donate gifts for community children in need. My tip? Head east before dusk to watch the moon rise over the beautifully lit Montauk Lighthouse. With its new coat of paint and newly restored Fresnel light—it’s truly a seasonal sight to see.  


Work With Bill

Whether it's knowledge about individual neighborhoods, schools, shopping, beach permits, building codes or where to go for approvals—I help my clients expertly navigate the region, even if they’ve lived here before. My clients are comfortable seeking my knowledge about any aspect of living in the Hamptons, not just real estate.

Follow Me on Instagram