– Santa sighting     – Tree lighting     – Admission cost

Event categories
Parades & festivals
Holiday open houses & tours
Craft shows & fairs
Plays & performance
Pet photos
Other events & activities

Parades and festivals

Greenport’s Parade of Lights and Christmas Tree Lighting (Greenport) 
Saturday, December 2, 5:00 p.m.
Parade begins at Center and Main Streets proceeds down Main to Mitchell Park for holiday songs, visit with Santa and Mrs. Claus, tree lighting.

Christmas in Cutchogue (Cutchogue)
Saturday, December 9, 9:30 a.m.
Annual holiday celebration in Cutchogue Village. Magic show at Cutchogue firehouse at 9:30 a.m. followed by Santa’s arrival by helicopter at about 10:30 a.m. Afterwards, follow Santa to the Cutchogue New Suffolk Library for photos. Free.

Riverhead Christmas Parade and Bonfire (Riverhead)
Saturday, December 9, Parade at 3 p.m., bonfire at 4 p.m.
The annual Lion’s Club parade will begin at the corner of Osborn Ave.at West Main Street and culminate at the Peconic River parking lot for the annual bonfire. The parade is open to participants of all churches, religious organizations, fraternal and service clubs. Guests are invited to take free photos with Santa in the town’s Gingerbread House. Free hot chocolate will also be served.

Santa Christmas Parade (Southold)
Saturday, December 16, 6 p.m.
Decorated fire trucks and Santa parade through Southold. Begins at Southold High School on Oaklawn Avenue and ends at the firehouse where kids can greet Santa and enjoy hot chocolate.

Holiday open houses & tours

Southold Historical Society Annual Candlelight Tour & Tree Lighting (Southold)
Friday, November 24, 3 p.m. – 6 p.m.
A delightful way to start the celebration of the holiday season. This is a magical time for our members, their families and the Southold community to come together to have some good old-fashioned fun visiting Santa in the barn and touring historic houses. Throughout the complex, there will be crafts, demonstrations, games, music, refreshments, an antique toy exhibit and caroling (4:30 p.m. – 5:30 p.m.). The lighting of the tree will take place in front of the Ann Currie-Bell House at 5 p.m. Museum Complex, 55200 Main Road, Southold.

Christmas in Mattituck at the historical society (Mattituck)
Saturday, November 25, 11 a.m. – 5 p.m.
Holiday Open House, tree lighting and caroling. Free refreshments. Children can visit with Santa between 3 p.m – 5 p.m. Tree lighting and caroling at 5:00 p.m. 50/50 raffle in the New Egypt schoolhouse. Tour the historic Tuthill House 11 a.m. – 5 p.m.. Free. Mattituck-Laurel Historical Society Grounds, Main Road and Cardinal Drive.

Home for the Holidays Show House (Southold)
Sunday, November 26 and Sunday, Dec. 3, 1 p.m. – 4 p.m.
The Ann Currie-Bell house will be transformed into an enchanting Christmas setting from the past, expertly decorated by Lori Guyer, owner of White Flower Farmhouse. Tickets are $10 and will be available at the door or in advance at the Prince building. Children visit for free. 55200 Main Road, Southold.

Railroad Museum of Long Island Holiday Open House (Riverhead/Greenport)
Saturday and Sunday, December 2 and 3 (Greenport) December 9 and 10 (Riverhead) 11:30 a.m. – 3 p.m.
Free Admission. Santa arrives at noon. Refreshments will be provided, along with gifts for good girls and boys. Do some holiday shopping at the railroad museum gift shop. Visitors have a chance to win a Lionel O-Gauge toy train set.

Eggnog and Cookies at the East End Seaport Museum (Greenport)
Saturday and Sunday, December 2 and 3 Noon – 5 p.m.

Cutchogue Holiday House Tour (Cutchogue)
Saturday, December 9, 11 a.m. – 3:30 p.m.
Festive and beautifully decorated homes will open their doors for The Cutchogue Holiday House Tour. Five stops in all. Four festive Bed and Breakfasts will be decked out in holiday cheer and decorations, each will feature tastings by local vineyards and tantalizing tidbits will be created by local restaurants. A portion of the proceeds benefit local charities. Advance ticket purchase is required. For information and tickets visit https://cutchogueholidayhousetour.com/

Oysterponds Historical Society Holiday House Tour (Orient)
Saturday, December 9, Noon – 4 p.m.
Features old and new homes in Oysterponds dressed in their seasonal finery. Tickets are on sale the day of the event at the Orient Congregational Church starting at 11:30 a.m. For event information, please call 631.323.2480. Tickets: OHS Members $25/ Non-members $30

What the Dickens? (Southold)
Saturday, December 9, 1 p.m. – 4 p.m.
Step into the ageless holiday setting inspired by the writings of Charles Dickens. Take a Christmas stroll through the festively adorned museum complex accompanied by a Victorian costumed guide. Interact with Dickens vignettes during your walk, making you feel as though you’ve leapt into the pages of a classic tale. Admission $10, free for children. 55200 Main Road, Southold.

Craft shows and fairs

Country Parlor Holiday Folk Art & Gift Show (Riverhead)
Friday, November 24, Saturday, November 25 and Sunday November 26, 9 a.m. – 3 p.m. (Sunday 10 a.m. – 2 p.m.)
The historic Naugles Barn at Hallockville is transformed into a winter wonderland filled to the brim with holiday delights! Free admission to the show plus holiday shopping specials at Miss Ella’s Gift Shop in the Hudson House. Craft demonstrations on Saturday and Sunday. The Country Parlor features all handmade gifts, holiday decor and treasures for everyone on your holiday shopping list. 6038 Sound Avenue, Riverhead.

Wooden Wonderland Holiday Craft Show and Sale (Riverhead)
Saturday, December 2, 10 a.m. – 4:30 p.m.
A family-friendly event featuring local handmade wooden items as well as other local artisans’ wares. Live woodworking and woodcarving demonstrations indoors and outdoors on the Great Lawn. The event includes local vendors, holiday arts & crafts, ornaments, home décor, rustic Santas and gnomes, unique handmade carvings and other wooden items, local artisan-crafted holiday and everyday gifts, handmade soaps, candles, hats & scarves, and much more. Suffolk County Historical Society, 300 West Main Street, Riverhead.

Southold Historical Society Holiday Fair (Peconic)
Saturday, December 2, 11 a.m. – 2 p.m.
Southold Historical Society’s annual fair and raffle. Local vendors and artisans will be showcasing unique holiday gifts for all. There will be a crafts room and face painting for children, and baked goods for munching in “a café”! Children can visit Santa and Mrs. Claus from 11am-2pm for festive photos. Photos and admission are free. At the Southold Town Recreation Center, 970 Peconic Lane, Peconic.

Plays and performances

A Christmas Carol: Live Family Theater (Greenport)
Saturday, November 25, 4 p.m.
Live theater presentation based on Charles Dickens’ “A Christmas Carol.” Free for all. Greenport High School auditorium.

Moya Strast Ballet Theater presents Scrooge (Riverhead)
Friday, December 8, 7 p.m.
Vail-Leavitt Music Hall, 18 Peconic Avenue, Riverhead
Choreographed by Cheryl Rain and danced by the talented ballerinas of Moya Strast Ballet theater, Scrooge the ballet will be a heartwarming performance for the whole family.

A Christmas Carol: A Live Radio Play (Greenport)
Sunday, December 10, 2:00 pm
Peconic Landing will present Joe Landry’s “A Christmas Carol: A Live Radio Play.” Admission is free. The Charles Dickens holiday classic comes to life as a live 1940s radio broadcast, complete with vintage commercials for fruitcake (extra-fancy), and the magic of live sound effects and musical underscoring. Peconic Landing Community Center. Free to all; registration required. https://peconiclanding.ticketleap.com/

Carols and Cookies at the Jamesport Meeting House
Friday, December 15, 6:30 p.m.
Dena Tishim will be back with her Riverhead High School Chamber Chorus to perform seasonal selections and lead attendees in a sing-along of popular carols, followed by cookies and mulled cider in the Lecture Room.  Suggested $5 donation for adults.   All children welcome. 1590 Main Road, Jamesport.

Harbor Bells: English Bell Choir Directed by Valarie Bellz (Greenport)
Friday, December 15, 7:30 p.m.
Traditional holiday favorites performed live by English handbell choir Harbor Bells. Some of the selected works this season will be: Good King Wenceslas, Joy to the World, Jingle Bells, It Came Upon a Midnight Clear, O Little Town of Bethlehem, and We Three Kings. Peconic Landing Community Center, Greenport. Free to all; registration required. https://peconiclanding.ticketleap.com/

The Night Before Christmas with Santa: Holiday Celebration at Brecknock Hall (Greenport)
Friday, December 15 , 6 – 7:30 p.m.
Bring your family and friends for a visit with Santa and a special reading of The Night Before Christmas. Enjoy hot apple cider and holiday caroling while crafting. Presented by Peconic Landing & The Brecknock Hall Foundation. Free to all. Brecknock Hall, Peconic Landing, Greenport. Registration required. https://peconiclanding.ticketleap.com/

Holiday Extravaganza: Celebrating the Holidays in Music and Song (Greenport)
Saturday, December 16, 2:00 pm
Singer, songwriter, producer Darren Ottati has chosen his favorite holiday musical numbers for this marvelous review. With fellow artists Jenifer DeMeo, Amanda Kuchinski, Ralph DAmbroses, Shannon DuPuis, and their five-piece band, these dynamic performers will surely put you in the holiday spirit. Don’t miss this memorable salute to our favorite time of year at its best. Peconic Landing Community Center | Free to all | Registration required. https://peconiclanding.ticketleap.com/

Southold Opera Holiday Concert
Saturday, December 16, 6:30 p.m.
Southold Opera and Southold Historical Society Holiday Concert with the French American Choir of New York and the Southold Opera Choir.

Brady Rymer and the Little Band That Could Holiday Concert (Southold)
Thursday, December 21, 7 p.m.
Southold Library presents a holiday concert featuring three-time Grammy Nominees Brady Rymer and the Little Band That Could, and some more special guests. This is a fundraiser benefiting the Library’s Renovation Fund. At the Southold High School auditorium. Tickets $20 or family four-pack $75. http://southoldlibrary.org/celebrate-renovate/

One Christmas Night (Riverhead)
Friday, December 22, 7:30 p.m.
One Christmas Night is a musical for the entire family. Proceeds will benefit the less fortunate. Tickets are $15 available at: http://lwfgc.tix.com/Schedule.aspx?OrgNum=4290&framed=true Living Water Church, 24 Shade Tree Lane, Riverhead.

A Candlelit Christmas
Friday, December 22, 7 p.m.
The fifth annual Candlelit Christmas is the North Fork’s newest holiday musical tradition, featuring the Corchaug Singers under the direction of William Roslak, as well as string players from the Red Door Chamber Players. Featuring works for organ, choir, soloists, and violin by composers Marcel Dupre, Sigfrid Karg-Elert, Richard Proulx, David Willcocks, John Rutter and others. There will be carols for all to sing, interspersed with poetry readings selected by Peggy O’Connor. Our Lady of Ostrabrama R.C. Church – 3000 Depot Lane. Doors open at 6:30. Free-will offering, suggested donation $20 per person.

Pet photos with Santa

Santa and Open House
Sunday, December 3, 12 noon to 3 p.m.
Open house at Kent Animal Shelter, 2259 River Road, Calverton. Complimentary refreshments. Santa with professional photographer taking portraits. A $10 donation per photo is requested. Donations of pet food, treats, toys and clean bedding will be gratefully accepted.

Holiday Pet Photos (Cutchogue)
Sunday, December 3, 1:30 – 3:30 p.m.
Registration requested. A 4×6” print in a photo folder card will be created while you wait. Digital versions will be available after the event for social media sharing. Materials fee: $10. Cutchogue New Suffolk Library.

Pet Photos with Santa (Riverhead)
Saturday, December 9, 10 a.m. – 3 p.m.
Come down with any pet, large or small for a free photo with Santa. Talmage Farm Agway, Osborn Avenue, Riverhead.

Pet Photos with Santa (Southold)
Saturday, December 9, 10 a.m. – 2 p.m.
A yearly Southold tradition. Come down with any pet, large or small for a free photo with Santa. Chick’s Agway, Youngs Avenue, Southold.

Hydrant Hotel Holiday Pet Photos (Riverhead)
Friday, December 15, 10 a.m. – 4 p.m.
Santa will visit the Hydrant Hotel to take free photos with pets and collect donations for RSVP Inc Animal Welfare & Rescue Group. Call to reserve a spot. Hydrant Hotel, Raynor Avenue, Riverhead.

Other events and activities

Magical Polar Express Trolley Ride (Riverhead)
Dates from November 24 – December 23
Inspired by the iconic film and award-winning book by Chris Van Allsburg, the magic of The Polar Express comes to life on a trolley ride where you will interact with characters from the story, then disembark and visit with Santa and his elves. Santa will present children with the first gift of Christmas. Finish the night with hot cocoa and cookies. For tickets visit https://www.northforktrolley.com/PolarExpress.php

Jamesport Christmas Tree Lighting 
Wednesday, November 29, 6:30 p.m.
Caroling under the gazebo at 6:30, followed by tree lighting. Santa arrives by fire truck to visit with kids in the community center. Bring your own camera.

Big Duck Holiday Lighting (Flanders)
Wednesday, Nov. 29, 7-9 p.m.
The festivities include a visit from Quackerjack along with duck carols led by the Middle School’s Show Choir along with refreshments and culminating with the arrival of Santa Claus by fire truck.

NSA Tree Lighting
Thursday, November 30, 5 p.m.
Songs by East End Church of Christ Children’s Choir. Visit from Santa Claus. Refreshments. NSA is located at 711 Union Avenue, Aquebogue.

A Christmas Story Celebration
Saturday, December 16, 7 p.m.
Come dressed as your favorite character from A Christmas Story. Lottery tree raffle, 50/50 raffle, food and fun. All proceeds benefit John’s Place Homeless Outreach and the North Fork Animal Welfare League. Admission $25. At North Fork Taps & Corks 53345 Main Rd #5, Southold.

Christmas Tree Lighting (Mattituck)
Friday, December 1, 7 p.m.
Santa and Mrs. Claus light the solar powered Christmas tree. Free hot chocolate, cookies. Christmas donkeys and caroling. The tree lighting will take place in Raymond F. Nine Park, Main Road, Mattituck (at the park in front of the CVS Pharmacy)

Santa Day (Mattituck)
Saturday, December 2, 10 a.m.
Festivities start at 10 a.m., when kids can see a free movie at Mattituck Cinemas. Afterwards they can have their picture taken with Santa and Mrs. Claus, who will arrive at Mattituck Plaza at 11:45 a.m. on a Mattituck Fire Department truck. Guests will be provided free hot chocolate from Starbucks starting at 11:30 a.m.

Gingerbread House Workshop (Cutchogue)
Saturday, Dec. 2, 1 p.m.
Your favorite gingerbread house building and decorating workshop at the Cutchogue New Suffolk Library. Fun for the whole family. Registration required. Space is limited.

Old Fashioned Tree Lighting & Carol Sing-Along (Cutchogue)
Saturday, December 2, 4:30 p.m.
The Village Green and its towering Christmas tree form the perfect backdrop for traditional family events. Caroling outdoors and tree lighting followed by free refreshments in the Old Schoolhouse. Santa is sure to stop by. Cutchogue Village Green.

Truth Community Church Tree Lighting (Flanders)
Saturday, December 2, 6 p.m.
Truth Community Church. Raffles and giveaways, pictures with Santa, Bonfire and desserts. Middle School Choir will perform. Fire Dept. and Flanders Northampton Ambulance will be there. 46 Bell Ave, Flanders.

The Spirit of Christmas (Riverhead)
Sundays, December 3, 10, and 17, 11 a.m. – 3 p.m.
Spirit’s Promise Equine Rescue presents The Spirit of Christmas. Visit with Santa, say hello to equine reindeer, story time, cookies, vendors, food trucks. Admission donation $25 adult, $5 child. 2746 Sound Avenue, Riverhead. http://www.spiritspromiserescue.org/

Truth Community Church Tree Lighting (Flanders)
Saturday, December 2, 6 p.m.
Truth Community Church. Raffles and giveaways, pictures with Santa, Bonfire and desserts. Middle School Choir will perform. Fire Dept. and Flanders Northampton Ambulance will be there. 46 Bell Ave, Flanders.

Breakfast with Santa
Saturday, December 9, 9 a.m. to 12 noon
Free pancake breakfast and visit with Santa. Bring your own camera for photos. North Shore Christian Church, 120 Kroemer Ave, Riverhead

North Fork Holiday Wrap-A-Thon (Peconic)
Saturday, December 9, 12 – 5 p.m.
Bring your holiday gifts and have them wrapped by volunteers! In return, a cash donation is requested, with all proceeds going toward CAST’s Holiday Toy Drive. Refreshments will be provided, along with entertainment by holiday carolers. Anyone interested in volunteering can email Donna at donnafiumano@gmail.com. Southold Town Recreation Department, 970 Peconic Lane, Peconic.

Cutchogue Fire Department Stuff the Sleigh 5K Race/Walk (Cutchogue)
Sunday, December 10, 10 a.m.
5K Race/Walk and children’s fun run to benefit the Cutchogue Fire Department Scholarship Fund, The Fire Fighters Cancers Support Network and the American Parkinson’s Disease Foundation. In addition to the entry fee, runners are requested to bring a new unwrapped toy that will be donated to Southold Town CAST. Entrants to the children’s fun run are requested to bring 2 items of non-perishable food
Registration, information

Breakfast with Santa  
Saturday, December 16, 9-11 a.m.
A pancake breakfast with Santa Claus for all children. Free. Bring your own camera. Living Water Church, Hubbard Avenue and Shade Tree Lane, Riverhead.

Menorah Lighting Ceremony, Peconic Riverfront (Riverhead)
Saturday, December 15, 5:30 p.m.
Hanukkah prayers and songs will be led by Rabbi Michael Rascoe if Temple Israel, Riverhead. Latkes and jelly donuts will be served at the temple following the ceremony.

Menorah Lighting Ceremony, Mitchell Park (Greenport)
Sunday, December 17, 5 p.m.
Hanukkah blessings and songs will be led by Rabbi Gadi Cappella of Temple Tifereth-Israel. Latkes and other holiday fare will be served at the temple following the ceremony. info@tifereth-israel.com

If you know about a holiday event that isn’t in this guide, email the date, time, location and a short description to katie@riverheadlocal.com.

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