Experience Holidays in the Hamptons: Your Guide to Festive Activities and Luxurious Stays This Holiday Season

Make this holiday season unforgettable with cozy gatherings, outdoor adventures, and a luxurious Hamptons retreat. The perfect place to create a memorable holiday, blending seaside escape with festive activities. From scenic hikes through vibrant autumn landscapes to local holiday events and cozy fireside dinners, there's no better setting for family gatherings and relaxation. Discover why now is the time to book your Hamptons vacation rental here and enjoy a holiday filled with warmth, elegance, and seasonal delights.

Here are some must-attend activities to elevate your holiday season:

48th Annual TURKEY TROT RUN FOR FUN

Turkey “Run for Fun” History - On Thanksgiving morning 1976, John Keeshan got together with some friends to engage in a morning run from the Village Green, to the Lighthouse, and then back again. Now an annual event, it is a Hamptons tradition!

Aperitivo Sunset Cocktails at Baker House 1650

Enjoy specialty sunset cocktails every Friday and Saturday at Baker House 1650, where curated drinks pair beautifully with sweeping views and a warm social hour in East Hampton.

Candlelight Fridays at Wölffer Estate Vineyard

Cozy up with a candlelit evening at Wölffer Estate Vineyard's Tasting Room. Seasonal pairings, a refreshed winter menu, and exclusive new wine and cider releases await. Specialty cocktails add a festive touch, making this a perfect way to start the weekend. Reservations are highly recommended.

Exploring the Trails of Stony Hill

Join the Peconic Land Trust for a guided hike through the fields and woods of North Amagansett. This moderate-paced walk is a serene way to connect with nature in fall's rich colors. Reservations required.

Docent-Led Public Tours at LongHouse Reserve

Explore 16 stunning acres of gardens and art at LongHouse Reserve with a docent-led tour that shares the history and inspiration behind its diverse collection. Reservations recommended.

The 85th Member Artists Exhibition at Guild Hall

Immerse yourself in the East End's art scene at Guild Hall's 85th Artist Members Exhibition, featuring over 300 works in various mediums by both established and emerging talents. It's a wonderful way to support and celebrate the vibrant local arts community.

Literature Live!: A Streetcar Named Desire at Bay Street Theater

Experience Tennessee Williams' iconic play *A Streetcar Named Desire* as part of Bay Street Theater's Literature Live series. Performances run from November 14 through December 1st.

The 4th Annual Holiday Makers Market

Kick off holiday shopping at this curated artisan market hosted at The Church in Sag Harbor. Enjoy unique items from home goods to jewelry, plus food trucks, a sing-along, and more.

NFL Sundays at The Clubhouse

Catch the big games in style at The Clubhouse in East Hampton, where you can enjoy great eats and drinks while cheering on your favorite team.

Wellness Monday: Healing Breathwork at The Church

Join a stress-relieving breathwork session with Celine Antoine to unwind after the weekend's festivities.

Thanksgiving Bingo at Rogers Memorial Library

A festive bingo game designed for younger children—perfect for a quick family outing over the holiday.

Visit the Hamptons Observatory

Hamptons Observatory (formerly known as Montauk Observatory) was established in 2005. Providing free, year-round, family-friendly educational programs that focus on science in general and astronomy in particular. Their in-person and virtual lectures are presented by renowned scientists, astronauts, authors, and academicians.

Holiday Dining, Markets, and Seasonal Activities

The Hamptons is known for its vibrant seasonal events, with Thanksgiving marking the beginning of holiday lightings, festive markets, wine tastings, and beautiful dining experiences at local vineyards and restaurants. Be sure to book early to savor everything the Hamptons has to offer this Thanksgiving

Lighting the Lighthouse

The fun begins at around dusk, with live, singalong holiday music from Sarah Conway and the Playful Souls, as we await the main event: the lighting of the light at around 5:15 PM! Enjoy delicious hot chocolate donated by Hampton Coffee.

The East End's Holiday Light Show

Bonac Festival of Lights is back for the 2024 holiday season! Hosted by The East Hampton Masonic Lodge, Star of the East No. 843, Bonac Festival of Lights kicks off the holiday season on Friday, November 29th. The walk-through display, now in its fourth year, features over 70 holiday-themed light displays. The family-friendly display will be open Friday and Saturday nights, every weekend through December 21st from 5:30 - 8 p.m.

Annual Southampton Holiday Kickoff and Parade of Lights

Enjoy the Annual Parade of Lights and tree lighting ceremony in Agawam Park on November 30th. Complete with holiday songs courtesy of VOSH and MOSH, a spectacular fireworks display, and, of course, a special visit with Santa on the steps of the Southampton Cultural Center.

Community Holiday Sing-Along & Holiday Market

The highly anticipated annual Holiday Makers Market returns to the Church Sag Harbor! Shop for holiday gifts or treat yourself to something nice - all while supporting local artisans this season. With over 20 unique artisans and makers curated by Susan Nieland, the market features selections from home goods, clothing, jewelry, and more. You'll be able to find a special handmade gift with ease!

Winter Welcome Day & Holiday Market

Adults, children, and families can experience everything the Parrish Art Museum offers. Enjoy free admission all day alongside free activities including art workshops for children and adults, docent tours of exhibitions on view, Imagination Play Project: creative play for people of all ages and abilities, and a holiday market featuring over 25 vendors of jewelry, ceramics, gifts, artisanal foods, and more!

Buckskill Ice Rink

This winter, take time for the festive season and lace up your skates at The Buckskill Ice Rink. The Buckskill Ice Rink is the only refrigerated, NHL regulation-sized, ice rink in the Hamptons. Not only is their rink beautiful and spacious but their cozy clubhouse is available for anyone who needs a break with some hot cocoa next to the fire.

Southampton Ice Rink

Offering ice skating no matter the weather conditions, Southampton Ice Rink is the only covered rink in the Hamptons and is open for public skating this holiday season. This holiday season, you have the opportunity to skate with Santa himself on December 18th and 23rd. Grab your tickets to hit the ice with Santa Claus. Hang out after the ice in one of their new, rentable igloos. With plenty of space to enjoy the holidays covered under the stars, cozy up with board games and hot chocolate.

Westhampton Beach Performing Center

Don't miss the holiday favorite, The Nutcracker, live at the Westhampton Beach Performing Center. Join the Peconic Ballet as they run their production of the Nutcracker. Telling the well-known story of Clara and her beloved Nutcracker Doll as they journey to an enchanted wonderland forest and into the Land of The Sweets, the Peconic Ballet is sure to delight. Watch this year's Peconic Ballet Theatre's production of “The Nutcracker” with an all-new cast this Christmas season.

Holiday Boat Parade & Viewing Party

A festive evening at Inlet Seafood Restaurant watching beautifully decorated boats sail by in the annual holiday parade. Grab your friends and family, bring some hot cocoa, and enjoy the twinkling lights and holiday cheer. It's the perfect way to get into the holiday spirit that also raises money for the Montauk Food Pantry.

3rd Annual Magic of Montauk Holiday Fair

This third annual event consists of a lit holiday path around the town green, featuring holiday gift vendors, hot cocoa contest, children's activities, festive treats, food trucks, beer and wine, live music, Santa meet and greet, and LIVE reindeer! Bundle up, grab your loved ones, and don't miss out on all of the magic Montauk has to offer!

John Jermain Memorial Library

This New Year's Eve, John Jermain Memorial Library has put together a unique and family-friendly game event to kick off the new year. Bring the kids and drop by the library from 11-4 to enjoy Giant Jenga, Giant Connect 4, Cornhole, board games, and more!

Whether you're here for the food, the festivities, or simply to unwind with family and friends, the Hamptons offers a warm, coastal haven this holiday season.