This weekend there’s a varied slate of events to choose from: holiday concerts from classical to rockabilly; ugly sweaters; winter walks and strolls; decorated Victorian houses and bed and breakfasts for you to explore; puppet making, crafts, and cookies for the kids; and plenty of opportunities to sip, shop, and sample tasty bites. Get some friends and family together and spend some time enjoying the season!
THURSDAY
Ugly Sweater Soirée | Alize Brewing Company, 10560 Main Road, Mattituck
From 6-10 p.m. on Thursday, wear your ugliest sweater to this free event while you enjoy live music and local vendors; food and drink available to purchase. For more information click here.
Speed Dating: Ugly Sweater Edition | Mugs on Main, 33 East Main Street, Riverhead
For ages 35-55, this event takes place from 7-9 p.m. (check in is from 6-7 p.m.). Meet new folks for quick conversations in a fun, safe atmosphere. Tickets are $25 and can be purchased here.
FRIDAY
NOMA Holiday Market Sip and Shop | North Main Street, Greenport
On Friday from 5-9 p.m., visit local businesses on North Main Street including Barbara Fisher Home, Demarchelier, Stirling Sake, Clarke’s Garden and more for special discounts, hot cocoa, festive drinks, mulled wine and music. Find more information here.
Cookies and Crafts with Santa Drop-Off | Southold Recreation Center, 970 Peconic Lane, Peconic
On Friday from 4-6 p.m., kids ages 5-10 may be dropped off for an evening of holiday crafts, cookies, and a holiday movie. Santa will read a story and take photos at the end of the session. Free; registration is required. Click here to register.
SATURDAY
North Fork Holiday Stroll | Throughout the North Fork
This North Fork Promotional Council event runs from 11 a.m.-6 p.m. on Saturday. Choose from four ticketed tours with timed slots to visit decorated bed and breakfasts, boutiques, restaurants, historical sites and wineries; wine tastings and small bites available at select stops. Tickets are $100. To view tours, list of participating businesses and to purchase tickets, click here.
Greenport Victorian Holiday House Tour | Sterling Historical Society-Ireland House, 319 Main St., Greenport
From 3-6 p.m., tour eight decorated Victorian homes plus the Little Red Schoolhouse and the Village Blacksmith; all proceeds go to the Sterling Historical Society. Tickets are $30 for members, $35 for non-members, and $40 at the door. For details and tickets click here.
Haven’s Holiday Farmers Market | Shelter Island Historical Society, 16 South Ferry Road, Shelter Island
Stop by this holiday market on Saturday from 10 a.m.-2 p.m. where you’ll find local food and beverage vendors, live music, handmade gifts, a food truck, storytime with the Shelter Island Library and more! Rain Date 12/15. Check here for more details.
“O Holy Night: The Silence and the Sound” Christmas Cantata | Mattituck Presbyterian Church, 12605 Main Road, Mattituck
Enjoy this free Christmas concert at 3 p.m. on Saturday. Space is limited with first-come first-served seating. For more information, click here.
Saturday Puppetry Workshop | Peconic Community School, 27685 Main Road, Cutchogue
This one-day workshop for grades 2-6 with Carmen Campos of Puppet ED runs from 10 a.m.-2 p.m. Cost is $125; click here to register.
Holiday Concert | North Fork Community Theatre, 12700 Old Sound Ave., Mattituck
The NFCT’s free annual holiday concert returns for two dates: Saturday 12/14 at 7:30 p.m. and Sunday 12/15 at 2:30 p.m. Sing along to your favorite holiday songs with talented theater alumni. For more information, click here.
SUNDAY
3rd Annual Holiday Mart | Lumber + Salt, 5570 Sound Ave., Jamesport
Sheri Winter Parker hosts this special holiday event benefiting ELIH Foundation from 11 a.m.–4 p.m. Purveyors include Pure Thread, Village Cheese Shop, TheSalting, The Treatery, Michelle Farrell Pottery and more. Bites available by Maize Empanadas, Tequila tasting by Casa J and Flavor Fork.
Classical Mandolin Concert with Andrew Joseph | Floyd Memorial Library, 539 First St., Greenport
Join this talented musician, composer and arranger for an afternoon concert of classical mandolin music from 3-4:30 p.m. Free; for more details click here.
Rockabilly Christmas | The Suffolk, 118 East Main St., Riverhead
Get your holiday groove on with this holiday concert featuring Jason D. Williams, Gene Casey and the Lonesharks, and The Vendettas on Sunday at 7 p.m. Tickets are $35-65 and can be purchased here.
