Entertainment

Filtering by: Entertainment
Nov
28
to Dec 19

Dickens Village Vignettes at The Carnegie Heritage Center

  • The Carnegie Heritage Center (map)
  • Google Calendar ICS

Experience a charming reimagining of a Vineyard favorite at the Carnegie Heritage Center: the annual Dickens Village, presented as Dickens Village Vignettes.  Peek into our reading-room “windows” and shelves to discover Dickens Village scenes—A Victorian Christmas in miniature! Suggested donation of $5. Regular business hours are Tuesday- Saturday, 10am-4pm.

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Dec
1
to Dec 14

Window Decorating Contest - We Need Your Vote!

  • Main Street Edgartown, MA 02539 (map)
  • Google Calendar ICS

Deck the halls and trim the trees, but don’t forget about Edgartown’s store front windows! Visit Edgartown is excited to share the 5th Annual Window Decorating Contest. The competition is sure to be fierce, which is why we need your help - vote for the People’s Choice Award before Sunday, Dec. 14th at 5 PM for the window that made your heart grow three sizes this Christmas In Edgartown! SUBMIT YOUR VOTE HERE

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Dec
11
to Dec 14

Town Bar MV Ugly Sweater Contest

  • Town Bar & Grill MV (map)
  • Google Calendar ICS

Break out your brightest, boldest, and downright ugliest holiday sweaters and join us for a weekend full of fun and festive vibes! From Friday through Sunday, guests are invited to show off their most outrageous holiday attire while dining with us.

Snap a photo in your ugly sweater during your visit and enter our Ugly Sweater Contest for a chance to win a restaurant gift card and a festive swag basket packed with goodies!

All participants will be entered into our weekend-long drawing, and the lucky winner will be announced on Sunday. Whether it’s sparkly, silly, or spectacularly tacky—we want to see it! Come enjoy great food, good company, and holiday cheer all weekend long.

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Dec
12
to Dec 14

Holiday at Donaroma's Glasshouse and Gardens

Stroll through our Garden Store and Nursery decorated for the holidays featuring the Land of the Northern Lights. Enjoy our festive set up and decor perfect for photos and holiday shopping. Featuring a large selection of ornaments, greens and gifts. Donaroma’s is a proud sponsor of Christmas In Edgartown.

Friday, December 12 - 9 am - 7 pm
Saturday, December 13 - 9 am - 5 pm
Sunday, December 14 - 10 am - 2 pm

Contact amy@donaromas.com for more information.

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Dec
12
to Dec 14

Martha's Vineyard Teddy Bear Suite

Celebrating its 15th enchanting year, the Martha’s Vineyard Teddy Bear Suite is a beloved holiday tradition where family memories are made. This magical event supports the Martha’s Vineyard Boys & Girls Club’s after-school food program, providing nutritious meals for hundreds of Island children and families while helping strengthen food security across the community.

Tickets must be purchased in advance to visit the MV Teddy Bear Suite. Admission is $5 per person + processing fees, with 100% of proceeds benefiting the Martha’s Vineyard Boys & Girls Club. Join us in spreading warmth, joy, and generosity this holiday season.

Teddy Bear Suite Hours:
Friday, December 12 | 2:00 PM – 6:00 PM
Saturday, December 13 | 12:00 PM – 6:00 PM
Sunday, December 14 | 10:00 AM – 2:00 PM

Advance tickets here |  Hosted by Harbor View Hotel & Point B | Compass

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Dec
12
to Dec 14

No Room in the Inn

“No Room in the Inn”
A display of Christmas Nativity Scenes at the Federated Church
For the benefit of Habitat for Humanity of Martha’s Vineyard

“There is no Room in the Inn” a display of Creches for the benefit of Habitat for Humanity of Martha’s Vineyard will be part of Christmas in Edgartown this December. For the fifth, the Federated Church Meetinghouse will be filled with over fifty cheches. These are miniature nativity scenes, which celebrate the birth of Jesus. Children are welcome and will go home with stickers of the nativity scene and a backdrop to color.

Because Bethlehem was full of travelers who had come to take part in the Roman census, there was no room in the inns for Joseph and Mary and their newborn child. Creches represent the stable where the family had to stay.

Many Island residents face the same problem that Mary and Joseph faced in Bethlehem. The Creche display seeks to raise funds for Habitat for Humanity of Martha’s Vineyard.
The Creches reflect the creativity of the artists who have made the individual scenes. They range in style from delicate creches made of fragile crystal and glass to the austere beauty of Haitian scenes crafted out of metal salvage from oil drums. There is a 60-year-old German creche fabricated out of cloth and glue which must be handled with care and others made out of wool and wood which a child can play with.

Habitat Director, Greg Orcutt, will be available to answer questions on both days. Elizabth Villarc, Church Historian, will also be available to answer questions about the Meetinghouse and the creches.

Friday December 12, 4:00PM- 6:00

Saturday, December 13, 11:00 AM-4:00PM

Sunday, December 14, 11:30-4:00PM

Contact evillardmv@gmail.com for more information.



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Dec
13
to Dec 14

Sweet Homes of Edgartown Gingerbread Houses

Celebrate the magic of Christmas in Edgartown at the Sweet Homes of Edgartown Gingerbread House Competition - a festive, family-friendly showcase where imagination is the only rule.

From classic cottages and island lighthouses to gingerbread cars, candy hot-air balloons, holiday scenes, and whimsical winter worlds, creators of all ages are invited to dream big. Build anything that tells a story… as long as it’s made of gingerbread and holiday spirit.

Visitors are welcome to wander through the display free of charge, enjoy hot chocolate and treats, and vote for their favorite creation. Donations benefiting the Martha’s Vineyard Animal Shelter are warmly encouraged.

Gingerbread Creation Drop-Off:

Friday, December 12 | 12:00 PM - 5:00 PM

All entries must be pre-built. Entry fee: $5 per creation, collected at drop-off.

Participants must register in advance using the event QR code.

Public Viewing Hours:

Saturday, December 13 | 10:00 AM - 3:00 PM

Sunday, December 14 | 10:00 AM - 3:00 PM

Winner Announcement:

Sunday, December 14 | 3:00 PM

Prizes awarded based on public voting.

Hosted by Mad Martha’s & Portfolio Properties MV

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Dec
13
3:00 PM15:00

Live Music Saturday at The Wharf Pub

Don’t let the fun stop! Enjoy a musical Saturday of festive performances. Johnny Hoy & Delanie Pickering with crowd favorites from 3 - 5 PM, followed Dock Street Fight Club high-energy from 9 - 12:30 AM. Contact 508-627-9966 for more information. The Wharf Pub is a proud sponsor of Christmas In Edgartown.

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Dec
14
11:00 AM11:00

African American Heritage Trail Martha’s Vineyard

Walking tour focusing on Edgartown’s history embracing the stories of enslavement and fugitives. Visit the church where Frederick Douglass exhorted the people of Edgartown to resist the Fugitive Slave Act and the Courthouse honoring Superior Court Judge Herbert A Tucker. The tour culminates at Memorial wharf where you will be blessed or cursed by Wise Woman Nancy Michael.

Meet at the Old Whaling Church at 11am, Friday and Sunday.

Call 508 524 8023 with any questions. Tour is brought to you by the African American Heritage Trail Martha’s Vineyard

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Dec
14
4:00 PM16:00

First Night of Hanukkah Menorah Lighting Extravaganza

Join us in the Edgartown Mini Park for a joyful community celebration as we welcome the first night of Hanukkah with the Chabad on the Vineyard.

Gather with friends, neighbors, and visitors for the ceremonial lighting of the menorah, uplifting music, traditional Hanukkah treats, and a festive atmosphere that shines with warmth and togetherness. All are welcome to share in the light, unity, and hope that this special evening brings.

Come celebrate the beginning of the Festival of Lights in the heart of Edgartown!

Hosted by Edgartown Board of Trade and Chabad on the Vineyard

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Dec
31
to Jan 1

DJ Felix NYE Party at Alchemy

Celebrate New Year's Eve in style! We can’t wait to welcome you to Alchemy, where we have two seating times available: 5:30 PM - 7:00 PM for a delicious three-course meal, and 7:15 PM - 10:00 PM for an exceptional four-course dining experience, click here for the menu. Be sure to catch our dazzling balloon drop and enjoy an amazing party with DJ Felix spinning your favorite tracks. Reservations can only be made by phone. We look forward to celebrating with you! Call 508-627-9999 for more information.

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Dec
13
4:00 PM16:00

Minnesingers Annual Family Holiday Concert with Santa!

Benefit concert for the Martha’s Vineyard Regional High School choral group, Minnesingers and Vineyard Preservation Trust. This is their 33rd year the Minnesingers have performed at The Old Whaling Church. Tickets $20.00; Students $15.00, Kids 12 & Under Free (must have a ticket to enter)

Doors open at 7:30. Please call 774-549-9107 with questions and visit https://vineyardtrust.org/events/ to reserve your tickets.

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Dec
13
2:00 PM14:00

Tides and Tastings at the Norton Boathouse

Step into Vineyard maritime history with a touch of holiday cheer! Join Vineyard Preservation Trust, MV Shellfish Group, and MV Vintage Wine & Spirits for a cozy afternoon by the waterfront featuring fresh oysters, expertly paired wines, and stories of the sea that connect shellfish and vine.

$65 per person
Tickets: https://auctria.events/Vptholiday

Contact leslie@mvpreservation.org for more information

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Dec
13
1:00 PM13:00

Buddy the Elf Breakfast Spaghetti Eating Competition

At the Annual Buddy the Elf Spaghetti Eating Competition, you’ll dive right in hands first to tackle a magical bag of spaghetti topped with maple syrup and M&Ms. 🍬

The first festive elf to finish wins a $200 gift card to Sea Legs — perfect for treating yourself after your sweet victory!

Grab your stretchy pants, bring your Christmas cheer, and join us for some sticky, syrupy, elf-approved fun.

Come hungry, leave jolly — and maybe a little sticky!

Contestants and spectators please gather on the street outside 13 Dock Street right before 1PM.

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Dec
13
1:00 PM13:00

Holiday Storytime with Author Cathryn Newton

Join the festivities at The Harborside Inn after the parade for a holiday reading/signing of HOME SWEET ISLAND by children’s author Cathryn Newton. This promises to be a special Christmas in Edgartown Event presented by The Harborside Inn with Edgartown Books.

About the Book: When Linnea learns of an impending winter storm stranding a ship, she quickly devises a plan to bring the island together. Much to her surprise, her compassion evokes holiday magic! Inspired by a community of islanders from Menemsha who braved high-running tides and the winter elements to bring Christmas cheer to a vessel from Europe that was stranded over the holidays in the harbor, the story is a heartwarming tale of true islander spirit and kindness.
About the Author: Cathryn Newton has always found inspiration living by the sea and finding the beauty in nature and art. Living on Martha's Vineyard for many years, she was captivated by the stories from lighthouse keepers, ship captains, and salt of the earth islanders. Cathryn wanted to share the magic of the island through children's books. She now resides in Rhode Island and the Vineyard with her family.

Contact events@theharborsideinn.com for more information.

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Dec
13
12:00 PM12:00

Candy Cane Lane in Nevin Square

Half way up Winter Street, you will find

A Square full of fun with kids in mind.

Candy Cane Lane is the new wonderland,

Featuring young merchants, activities, and treats - you must experience firsthand!

See all that is planned at Candy Cane Lane here!

Candy Cane Lane is brought to you by the Nevin Square Association, with help from their amazing businesses.

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Dec
13
12:00 PM12:00

Very Vineyard Vin Chaud

  • Dr. Daniel Fisher House & Gardens (map)
  • Google Calendar ICS

Join the MV Chamber of Commerce for a warm and festive holiday experience in downtown Edgartown! Sip our French-inspired Vin Chaud—traditional mulled wine, warmed and spiced—served in a custom Very Vineyard Holiday commemorative cup you can take home. Step into our cozy holiday lounge, transformed into a charming winter wonderland complete with glowing décor, inviting seating, twinkling lights, and festive photo moments. A beautifully decorated, heated tent creates the perfect backdrop to relax, mingle, and enjoy the magic of the season.

As you soak in the holiday atmosphere, enjoy live musical performances by Martin & Kelly and CJ Solar from 1–3 PM, filling the afternoon with joyful cheer. Guests will also receive Golden Tickets for our Island-wide Very Vineyard Holiday Giveaway—your chance to shop local and win big.

Come get cozy, feel the magic of Christmas in Edgartown, and savor a warm cup of Vin Chaud with us! Special thanks to this event’s generous sponsors: Vineyard Preservation Trust, Vintage MV Wine & Spirits, KG Events & Design, Drinks on MV, Jardin Mahoney, Serena & Lily, Tilton Tents, Tracker Home Decor, Vineyard Hearth Patio & Spa, Free People, Hospice and The Black Dog.

The Martha’s Vineyard Chamber of Commerce is a proud sponsor of Christmas In Edgartown.

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Dec
13
12:00 PM12:00

Open House at Morning Glory Farm

Morning Glory Farm will be hosting our annual Open House at the Farm from 12-3pm.

There will be hayrides in our fields, make your own s'mores by the firepit, lot's of eggnog, light refreshments, appetizers including fresh vegetables from our farm paired with housemade dips and local cheese and fruits.

Our kitchen is highlighting our very own corn chowder this year and our bakery will have Christmas treats including Bushe de Noel. Raffles and more.

Everything above is complimentary.

You're invited to join us during our 50th Anniversary year at Morning Glory Farm!

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Dec
13
11:45 AM11:45

Little Gems Show with Jazz by Jeremy Berlin

Eisenhauer Gallery looks forward to hosting a small gems exhibition following the Christmas Edgartown parade on Saturday. This show will be accompanied with Jazz by Jeremy Berlin and fresh collections from favorite artists. Warm up with a cup of cider or tea with good company!

Contact 508-627-7003 or eisenhauergallery@gmail.com for more information.

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Dec
13
11:45 AM11:45

Photos with Santa sponsored by Wallace & Co

Sponsored by Wallace & Co. Sotheby's International Realty, Santa will be arriving at The Covington Restaurant at 52 Main Street in Edgartown following the parade. Santa will be available for photos from 11:45 AM - 1:00 PM. Use your own camera, no charge. Donations will be accepted to benefit the Red Stocking Fund. Contact 508.627.3313 or info@wallacemv.com for more information.

Wallace & Co. Sotheby's International Realty is a proud sponsor of Christmas In Edgartown.

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Dec
13
11:45 AM11:45

Grinchmas in Edgartown

Welcome to Grinchmas in Edgartown presented by the Island Autism Group and sponsored by Vineyard Dream Realty LLC, Grinchmas in Edgartown promises to be a festive and heartwarming event for the entire community.
Meet the Grinch and Friends: Capture the magic of the season by taking a picture with the Grinch himself and his whimsical friends.
Sweet Treats: Indulge in delightful sweet treats that are sure to please both young and old alike.
Christmas Merchandise: Purchase Christmas merchandise. All proceeds from the sales will benefit the Island Autism Group.
Vineyard Dream Realty LLC is a proud sponsor of Christmas in Edgartown.

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Dec
13
11:30 AM11:30

No Mess Gingerbread House Kits

Waterfront Builders will be handing out free no-mess gingerbread house kits for families to take and complete at home! Supplies are limited. Waterfront Builders is a proud sponsor of Christmas in Edgartown.

For more information contact mikaela@waterfrontbuildersmv.com

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Dec
13
11:00 AM11:00

Tides & Tastings at Norton Boathouse

Step into Vineyard maritime history with a touch of holiday cheer at the Norton Boathouse! Join Vineyard Preservation Trust, MV Shellfish Group, and MV Vintage Wine & Spirits for a cozy, flavorful afternoon by the waterfront. Savor fresh Island oysters paired with expertly selected wines, and explore the fascinating science that connects sea and vine.

Discover the stories of the working waterfront while twinkling lights and seasonal touches set the mood. Come celebrate the season—and the Vineyard’s rich coastal traditions—in a gathering that’s as delicious as it is enlightening. Time: 2 classes, 11 am and 2 pm

Tickets: $65 | visit https://vineyardtrust.org/events/ or call 508–627–4440

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Dec
13
10:30 AM10:30

Make Your Own Wrapping Paper at Edgartown Library

Stop by the Children's room to make your own wrapping paper. We will provide all the supplies, just bring your creativity. Drop in 10:30-3. Children under 8 must be accompanied by an adult caregiver.

Contact elyce@edgartownlibrary.org for more information.

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Dec
13
10:00 AM10:00

Plum Hill School Annual Elves Faire

The Elves Fair is back to benefit the Plum Hill School, a Christmas in Edgartown tradition. Make your own gingerbread houses, beeswax candles and more. Warm up with lunch at our Elves Cafe & visit our Waldorf Gift Shop for handmade toys and books. The silent auction is now digital so there is more room for crafting, eating, shopping and enjoying the holiday spirit together. Please email hello@plumhillschool.com with questions.

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Holiday Faire in the Edgartown Village Green
Dec
13
10:00 AM10:00

Holiday Faire in the Edgartown Village Green

Brought to you by the Edgartown Village Market, the Holiday Faire is back and right in the heart of our downtown winter wonderland. Make s'no mistake, this is an absolute must-do event! Join us in the Village Green to shop one-of-a-kind artisanal goods from over 30 local vendors in this European-style Christmas market complete with hot cocoa, treats, and entertainment for the whole family. Warm up in the tented beer garden while listening to live music and enjoying an array of seasonal food and drinks. Libations will be available for purchase to benefit local non-profits. 

Participating artisans coming soon

Thank you to our Holiday Faire partners: Vineyard Preservation Trust, Edgartown Village Market, Donnelly + Co, Amity Island Running Club & Wash Ashore Beer Co. , and Foley Family Wines.

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Dec
13
10:00 AM10:00

A Cooke House Christmas Experience

Step back in time and celebrate the season with A Cooke House Christmas Experience during Christmas in Edgartown! Join us at the MV Museum’s historic Cooke House property on School Street from 10am to 2pm for a cozy holiday gathering filled with cheer, tradition, and community spirit.

Enjoy a cup of hot cocoa and a sweet treat while you play “Shut the Box” or work on a puzzle, shop some of the Museum Shop’s most popular items, perfect for gifting (or keeping for yourself!). Purchase a raffle ticket for a chance to win a Museum Shop Gift Bag, brimming with local treasures.

Admission is free and donations are gratefully accepted.

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Dec
13
10:00 AM10:00

Elf on the Shelf Scavenger Hunt at The Carnegie Heritage Center

Join the fun with our classic Elf on the Shelf Scavenger Hunt amongst Carnegie's historic artifacts! Kids of all ages follow clues, search for elves, and win exciting prizes! Warm up with our Hot Chocolate Cart—complete with all your favorite toppings! Please call 508–627–4440 with your questions.

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Dec
12
8:00 PM20:00

Minnesingers Annual Family Holiday Concert

Benefit concert for the Martha’s Vineyard Regional High School choral group, Minnesingers and Vineyard Preservation Trust. This is their 33rd year the Minnesingers have performed at The Old Whaling Church. Tickets $20.00; doors open at 7:30. Please call 774-549-9107 with questions and visit https://vineyardtrust.org/events/ to reserve your tickets.

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Dec
12
6:00 PM18:00

Edgartown's Champagne Stroll with Banshee Sparkling Wines

Kick off your festive Friday night with our annual Champagne Stroll, featuring Banshee Sparkling Wines. Wander through downtown and visit select retailers offering complimentary bubbles while you shop. Sip, stroll, and discover holiday gifts while enjoying a sparkling start to the Christmas in Edgartown weekend.

Participating Retails: Eisenhauer Gallery, Sea Legs, Nell, Nell Home, Salte, Slate, Edgartown Books, Past & Presents, Juniper

Banshee is a proud sponsor of Christmas In Edgartown.

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Dec
12
6:00 PM18:00

Book signing with Julia Blanter

Join us for a book signing upstairs at the store with Julia Blanter, author of The Martha's Vineyard Cookbook.
It may be December, but you can celebrate summer any time of year with The Martha’s Vineyard Cookbook. The edible tour of the island’s six towns has curated the flavors of 100 island recipes while offering stunning, immersive photographs from America’s summer home destination.
With mouthwatering recipes from the restaurants, farmers, fishermen, and food artisans who make the Vineyard so vibrant, unique, and utterly delicious, the cookbook showcases both the iconic and the hidden delights of the island. From ArtCliff Diner’s warm Blueberry Buttermilk Scones to a refreshing Agricultural Fair-favorite Espresso Float, there’s something new and exciting to discover on every page.
Julia Blanter is a year-round Martha’s Vineyard resident with deep connections to the island’s culinary community. With extensive experience across the food industry, including head of marketing at New York’s legendary Fulton Fish Market, Blanter’s love of food has taken her into kitchens and restaurants all around the world. Born in the colorful, multicultural landscape of Sydney, Australia, Julia has lived in New Caledonia, the Netherlands, London, Brooklyn, and most recently, her island home of Martha’s Vineyard.

Email mtombers@edgartownbooks.com for more information.

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Dec
12
5:30 PM17:30

Vineyard Preservation Trust's Holiday Cocktail Party at The Carnegie

Join us at the festively decorated Carnegie Heritage Center and enjoy fine libations, delicious hors d’oeuvres, and holiday cheer in a charming, historic setting with friends of Vineyard Preservation Trust. $100 per person, please visit https://vineyardtrust.org/events/ to reserve your tickets.

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Dec
12
5:00 PM17:00

Live Music by Martin & Kelly and CJ Solar at Harbor View Hotel

Join us on Friday, December 12th, for a festive evening at the Harbor View Hotel, featuring live music by country stars Jill & Ryan of Martin and Kelly, performing alongside CJ Solar. Enjoy their performances before and after the Lighting of the Lighthouse, as well as following dinner in Bettini Restaurant. Move to the beat of their signature hits blended with heartwarming holiday classics as they fill the night with music. Celebrate the magic of the season with an unforgettable night of music, dining, and holiday cheer. The event is designed as a standing-room experience.
Seating is limited to hotel and restaurant guests. More info. Contact 508-627-7000 for more information. Harbor View Hotel is a proud sponsor of Christmas In Edgartown.

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