Here on the East End, December settles in softly—harbor lights flicker on at dusk, farm stands turn into Christmas markets, and every errand somehow feels a little more festive. There’s plenty to do (and wear) without overthinking it so we pulled together a few simple, can’t-miss ideas.
Before we dive into what to do this month, a quick recap from our weekend in Sag Harbor.
Sag Saturdays Recap + Invite
Thank you to everyone who popped by our first Sag Saturdays—we loved the neighborly drop-ins, warm hellos, and easy gifting that happened all afternoon.
Sag Saturdays returns Saturday, January 10th, with a wellness-minded event at our Sag Harbor store. Save the date; we’d love to see you.
Leallo Sag Harbor | 83 Main Street
P.S. Sample Sale—Amagansett (In-Store Only): We’re keeping the fun going this holiday season. We are running a sample sale at our Amagansett location through January with select one-of-a-kind pieces and past-season finds while they last.
Now—with your calendar open—here are the East End happenings to add to your holiday lineup.
Calissa Chalet, Water Mill
Water Mill’s Greek escape trades beach nights for alpine charm—think candlelit tables, mulled wine, and a winter, family-style menu that’s perfect for lingering with friends. Mediterranean classics get a cozy, cold-weather twist, and the room hums like a holiday house party.
Our Look: Alpaca Cocoon Cardigan + Dune Crop Pant
Calissa Chalet, Calissa’s après-ski-inspired lounge
Greenport Holiday Stroll & Harbor Front Night Market
Friday, December 19, 2025 • 5–8 PM • Greenport Village
Greenport glows for one festive night—Front and Main Streets lined with makers, music, and twinkle-lit shop windows. Start at the Harbor Front Inn lobby to grab the event booklet (map + offers) and a Holiday Bingo Card with 24 village stops. Pop into galleries, sip seasonal cocktails, snap a few photo ops, and circle back for the curated Night Market at the Harbor Front Inn, The Menhaden, and Little Creek’s Hold Fast Studio—think local jewelry, chocolate, and handcrafted gifts.
Our Look: Havens Cashmere Pullover, Ashley Barrel Pant, + Bay Street Cashmere Zip Up (to layer)
Downtown Greenport Village
Winter Wonderland, Wölffer Estate Vineyard
Sundays, December 21 & 28 • 11:00 AM–2:00 PM • Sagaponack
Step into the magic of the holidays at Wölffer Estate as the Tasting Room transforms into a market-inspired Winter Wonderland. Expect festive food and beverages, cozy firepits, and family-friendly fun: wander the Tasting Room & Terrace, meet Santa for cheerful photos, shop special gifts, get creative with kids’ crafts, enjoy live music, and savor delicious bites.
Our Look: Montauk Cashmere Cable Crew + Tasha Cashmere Pant
Eat, Drink, & Be Sparkling, Sparkling Pointe
Saturday, December 20 • 12:00–4:00 PM • Southold
Ring in the season with bubbles and bites at Sparkling Pointe’s holiday tasting. Seven sparkling wines are paired with a “feast of seven fishes” — locally sourced seafood small plates — for an afternoon that feels celebratory and distinctly North Fork.
Our Look: Lulu Blouse + Lulu Wide-Leg Pant (for a polished look with an elastic waist-perfect for a feast)
That’s our short list for a cozy December on the East End. If you’re nearby, pop into our stores for easy gifting (and try on something soft while you’re here). In Amagansett, our Sample Sale runs through January.
Shopping from home? Explore the Holiday Gift Guide for Leallo pieces that are simple to give and even better to keep.
Happy holidays from the Hamptons!
xx
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