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Holiday Happenings in the Sullivan Catskills

Holiday Happenings in the Sullivan Catskills

Tis’ the season to be jolly in the fa-la-la-la…Sullivan Catskills. Experience the charm of small-town fun with holiday tree lightings, Santa visits, ugly sweater parties, caroling, crafts, shopping – the list goes on. Pull out your planner, text your tribe, the holidays are happening here in the Sullivan Catskills. Find a place to stay, eat and explore – we’re waiting for you!


Jeffersonville’s Home for the Holidays

25th Annual James Dworetsky Holiday Parade • Friday, November 29, 7pm
Enjoy Main Street, all lit up with festive floats and the sounds of Christmas. Parade starts at 7pm. Santa will be at the Jeffersonville Firehouse, 4 to 9pm. At 5pm, Jeff Junction will have hot chocolate, cookies and Santa’s mailbox for children to mail their letters.

First Annual Holiday Market • November 29 & 30
The Holiday Market starts with a visit from Santa at 4pm on Friday, November 29th. This free event continues until 9pm on Friday and begins again on Saturday, the 30th from 11am to 4pm. The Market will be held in the Jeffersonville Firehouse on Main Street.

Ugly Sweater Party at Tavern on Main • Friday, November 29
Rock your ugly sweaters for a chance to win a gift certificate – and bragging rights.

Santa and His Elves Visit Jeff Bank • Saturday, November 30 • 12:30-3:30pm
Visit with Santa and have your photo taken. Free crafts for children to take home. Hot Chocolate and Cookies. $4.00 suggested donation for photos – all proceeds benefit the local food pantry.

Gingerbread Decorating for Children • Wednesday, December 4 • 4-5pm
Bring the kids to the Jeffersonville Branch of the Western Sullivan Public Library for a fairytale and gingerbread cooking decorating.

Food Tasting at Jeff Junction – Saturdays thru December 24

50% Off Santas at The Secret Garden Gift Shop – while supplies last.

Black Friday at Catskill Brewery

Friday, November 29 • 12-9pm
Join the folks at Catskill Brewery for a very special nightshine cask tasting, food from the Catskill Food Truck and holiday crowler deals – 4 for $30!

Callicoon’s 4th Annual Holiday Tree Lighting

Friday, November 29 • 5:30pm
Kick-off the holiday season with a tree lighting, bonfire, hot cocoa and s’mores for the kids in Callicoon on the Delaware.

Dance of Lights

Nightly, November 29 thru December 24 • 7pm
Don’t miss a fabulous holiday light show synchronized with music, nightly at Canal Towne Emporium in Wurtsboro.

Rock Hill Holiday Lighting

Sunday, December 1 • 5:30pm
Join the Rock Hill Business & Community Association for their annual tree and menorah lighting. Complimentary refreshments, live music after the lighting, plus visits from Santa and Mrs. Claus.

Jersey Tenors Holiday Show

Tuesday, December 3 • 1-4pm
Get into the holiday spirit with a fun-filled show featuring holiday classics at the Villa Roma Resort & Conference Center. Tickets include lunch and concert. Call Kelly Mullally at 845-887-5014 to make reservations.

Bethel Annual Tree Lighting

Friday, December 6 • 7-8pm
Head to the Town Square in Kauneonga Lake where you’ll await Mrs. Claus’ arrival by firetruck. Enjoy caroling, hot cocoa, treats and craft making for the kids at the Annual Tree Lighting in Bethel.

Holiday in Hurleyville

Saturday, December 7 • 11am-8pm
Head to Hurleyville to start your holiday shopping! Shop Hurleyville General Store for hand-selected and locally-made artisan goods; Hurleyville Market offers specialty coffee, teas, Thanksgiving Farm products, and more; Gallery 222 Pop-Up Shop and Exhibit features the work of local artisans, all available for purchase; Fiber On Main and Buck Brook Alpacas Pop-Up Shop will offer sweaters, socks, yarn, weaving looms, and gift certificates. Listen to live music along the Rail Trail, visit the Buck Brook Alpacas at the Firemen’s Park.

Come hungry, The Pickled Owl will be serving vegan chili, soup, and their take on the Sullivan County classic, “roast pork on garlic bread” straight out the kitchen door. Plus, food and drink specials inside for brunch and dinner with live music during the afternoon and evening hours. The Catskill Brewery Food Truck will serve up hearty burritos, and their award-winning brew. SUNY Sullivan Catskills Hospitality Institute will offer holiday cookies and sweet treats made by their culinary students.

Lunch with Santa in Narrowsburg

Saturday, December 7 • 11:30am-1pm
Bring the kids to Narrowsburg for a free lunch with Santa! Kids can enjoy hot dogs, mac and cheese, grilled cheese, chicken stew, crafts, cupcake decorating and photos with Santa. Adults are just $5 each.

An Afternoon with Santa at Hector’s Inn

Saturday, December 7 • 1-4pm
Santa returns to Hector’s Inn! Bring a wrapped gift for your child with their first and last name (you can drop it off early), Santa will call your child up to get their gift – the perfect opportunity for loads of photos. The kids can visit with live animals, have their faces painted and get temporary tattoos too.

Christmas Magic on Main Street Narrowsburg

Saturday, December 7 • 2-6pm
Meet on the observation deck in Narrowsburg for their annual tree lighting, horse-drawn carriage rides, cocoa, coffee, treats, professional photos with Santa, live music, and caroling – free for all!

A Messiah Sing-Along and Festive Party

Saturday, December 7 • 4-7pm
Join the Sullivan County Chamber Orchestra for a “Messiah Sing-Along“, festive party, crafts fair, and a special presentation by Nesin Cultural Arts students. Advance tickets encouraged limited availability at the door.

Murder Mystery: Santa’s Slay

Saturday, December 7 • 6-9pm
Not everyone plays nice and one unfortunate soul winds up dead! Find out who the naughty one is at a festive murder mystery dinner at Burn Brae Mansion.

Barryville Tree Lighting

Saturday, December 7 • 6-7:15pm
Share in the good cheer with goodies, hot chocolate, carols, and photos with Mr. & Mrs. Claus at the 14th Annual Barryville Tree Lighting. This is a free event, all are welcome. Event takes place in the cul-de-sac at the intersections of Route 97 & 55.

Ornament Make & Take

Sunday, December 8 • 11:30am
Grab your gal pals for an afternoon of crafty fun making ornaments at Tavern on Main. Choose your colors and design, sip champagne. Reserve your spot by calling Jessica at 845-482-2380 or

Monticello Holiday Event 2019

Sunday, December 8 • 4-7:30pm
Join the Monticello Chamber of Commerce at the Ted Strobele Recreation Center for a holiday movie, hot cocoa, cookies, letter writing to Santa and a visit from the Santa Express.

Rag Tree DIY

Wednesday, December 11 • 6pm
Bring your bestie to Tavern on Main for an evening of crafting and sipping on sangria. Reserve your spot by calling Jessica at 845-482-2380 or

Breakfast with Santa

Saturday, December 14 • 9am-12pm
Bring the kids to Catskill Mountains Resort for Breakfast with Santa. Afterward, help Mrs. Claus in the kitchen while baking her favorite cookies.

Dickens on the Delaware

Saturday, December 14 • 12-6pm
A Victorian holiday wonderland! The town of Callicoon will be bustling with holiday goods and shopkeepers dressed in Victorian garb for Dickens on the Delaware. Take a horse and buggy ride, sip hot cocoa, eggnog, mulled wine and more.

The Gingerbread Experience

Saturday, December 14 • 12-4pm
Stroll through the Liberty Museum & Arts Center for a gingerbread house exhibition, holiday craft show, bake sale, and ornament workshop. Admission is free.

Town of Neversink Annual Tree Lighting

Sunday, December 15 • 5-8pm
Begin your time in Neversink at The Daniel Pierce Library’s Holiday Tea from 1 to 3pm. Listen to Tri-Valley Central School students and community members as they sing and play instruments for a festive sing-a-long. Then, stay with all the “little elves” in your family for the Parks & Recreation Dept. Elf Workshop from 3:30 to 5pm where they’ll be making special holiday gifts. At the Tree Lighting, enjoy hotdogs, hamburgers, cocoa, cookies, s’mores and popcorn – free for all! Santa & Mrs. Claus will be visiting too.

Holiday Fun on the Farm

Saturday & Sunday, December 21 & 22 • 11am-12pm
Celebrate the winter solstice at Apple Pond Farm. Cozy up with the goats and sheep, listen to stories and sip hot cocoa. Dress warmly and RSVP if you’re planning to attend. Call or email, (845)482-4764,

The Santa Express

Dance and sing with Santa and all his North Pole friends. For 15 years, The Santa Express has been spreading joy to children and adults alike throughout the Sullivan Catskills. Fully equipped with a Christmas “Spirit Meter” to create Christmas magic in each town, Santa’s 50-foot sled beams with bright holiday lights, music and a Christmas scene like no other. Kids should bring their letters to put in Santa’s mailbox.


Saturday, December 7: 
5pm • Main Street, Liberty
7pm • Veterans Park, Bethel

Sunday, December 8
5pm • Senior Center, South Fallsburg
6:30pm • Recreation Center, Monticello


Saturday, December 14
5:30pm • 4 Corners, Yulan
6:30pm • Santa’s Village – Corner Piazza, Eldred
7:30pm • Lumberland Town Hall, Glen Spey

Sunday, December 15
5pm • Main Street, Jeffersonville
7pm • Narrowsburg Union, Narrowsburg


The Farmhouse Project Pop-up Shop

Friday-Sunday thru December 22 • 11am – 7pm
Shop The Farmhouse Project Pop-Up Shop in Livingston Manor for their new winter collection of table linens, dinnerware, candles and other curiosities, all made locally in Upstate, NY.

Wurtsboro Arts Alliance Holiday Show

Saturdays & Sundays thru December 21 • 12-4pm
Shop the Wurtsboro Arts Alliance Holiday Show for affordable gifts made by local artists. You’ll find pottery, ceramics, jewelry, photos, ornaments, greeting cards, and so much more.

Handmade for the Holidays

Saturday & Sunday, November 30 & December 1, December 7 & 8, December 14 & 15 • 11am-5pm
Find your way to Duke Pottery for their 13th Annual Handmade for the Holidays featuring 30+ artists and makers. Plus, you’ll find the largest array of pottery made by potter/owner, Carolyn Duke.

Holiday Pop-Up Shop with Buck Brook Alpacas

Thru December 24 • Mon-Sat 11am-6pm, Sun 11am-4pm
Find everything alpaca, plus provisions and gifts from local makers at Buck Brook Alpacas Holiday Pop-Up Shop.

IndieMart Narrowsburg

Friday thru Sunday, December 6-8 & December 13-15
IndieMart Narrowsburg features an array of local artists with unique and one-of-a-kind wares. Shop 20+ vendors each weekend upstairs at the Delaware Valley Arts Alliance Recital Hall.

10th Annual Holiday Market at Bethel Woods

Saturday & Sunday, December 7 & 8 • 11am-4pm
Gather in the Market Sheds at Bethel Woods Center for the Arts for their 10th Annual Holiday Market. Shop for local libations, fine arts and crafts, specialty foods – over 85 vendors! Enjoy 50% off Museum visits, a holiday craft studio, holiday caroling, photos with Santa and the lighting of the dove.

Holiday Artist & Craft Market at Gallery 222

Saturday, December 7 • 1-7pm
Art, crafts, gifts and more created by talented local artists and artisans. That’s what you’ll find at the Holiday Artists & Craft Market at Gallery 222 in Hurleyville.

Holiday Shopping Event

Saturday, December 14 • 12-5pm
Pick up great gifts for that special someone on your list at Catskill Mountains Resort annual holiday shopping event.

Sip, Shop and Spa

Saturday, December 21 • 9am-10pm
Visit Crystal Life Spa at Resorts World Catskills to sip champagne, shop, and sample spa services.

Holiday Movies

Frozen 2

Hurleyville Arts Centre thru December 8

Callicoon Theater thru December 12

The Polar Express

Henning’s Local – Monday, December 16 • Restaurant Opens at 5pm, Movie Starts at 6pm

Holiday Themed Weekend Getaways

Family Time at Frost Valley

December 6-8 & December 27 thru January 1
Spend quality time with the kiddos this holiday season during the International Festival of the Holidays or Holiday Family Camp. Enjoy the winter scenery while cross-country skiing or sliding down the tube run. Indoor activities include archery, the climbing wall, and winter-themed arts and crafts. In the evenings, keep cozy and warm by the fireplace with a cup of hot cocoa.

Christmas Celebration

Sunday thru Saturday, December 22-28
Enjoy this magical season with family and friends at the Villa Roma Resort & Conference Center. Enjoy visits with Santa, an eggnog party, nightly entertainment, children’s programs, skiing, snow tubing and more.

Dove Holiday Happiness Contest

As you travel the roads of the Sullivan Catskills this holiday season, you’ll be greeted by doves almost everywhere you go. Slow down; take a selfie. Enter our Dove Holiday Happiness Contest for your chance to win a Sullivan Catskills swag bag and gifts from the Sullivan County Democrat newspaper. Starting December 13 through January 31, you can submit your photos to Special consideration will be given to contestants who are creative and think outside the box; incorporate the spirit of the holiday season; include the Sullivan Catskills Visitors Association logo in their photo.

As for the rules and fine print, all submitted photos will be the property of the Sullivan Democrat and SCVA; photo submission automatically gives the Democrat and SCVA permission to use photos on the internet and for print, listing names of all individuals in photos; provide contact phone and address in email submission; no more than three photo submissions allowed.

New Year’s Celebrations

Electric Magic New Year’s Eve Celebration at Cabernet Frank’s

Tuesday, December 31 • 9pm-1am
Kick-off 2020 with live music and good times at Cabernet Frank’s.

New Year’s Eve Masquerade at The Sullivan Events Center

Tuesday, December 31 • 9pm-1am
Break out your masks, put on your best duds – the New Year’s Eve celebration at The Sullivan includes a five-hour open bar, four dinner stations, three dessert stations, DJ Corey Gips, a champagne toast, fun and lots of memories.

New Year’s Eve Party at Callicoon Brewing Co.

Tuesday, December 31 • 10pm
Ring in the new year with friends new and old at Callicoon Brewing Co. Watch the ball drop on the big screen, enjoy a midnight toast.

New Years at The Kartrite

Kick-off 2020 with a different adventure at The Kartrite Resort & Indoor Waterpark. On New Year’s Eve, the waterpark is open till 1am! Enjoy passed hors d’oeuvres, drink specials, champagne toast, giveaways, a DJ and watch the ball drop on multiple big screens.

Ring in 2020, Catskills Style!

Join Foster Supply Hospitality: The Arnold House, The North Branch Inn, Nine River Road, or The DeBruce for a special New Year’s celebration – Catskills style.

New Year’s Eve 2020 at The Western

Celebrate the New Year in style at The Western Supper Club & Inn. Feast on a 5-course dinner while cabaret jazz serenades you. At 8pm, the dance party starts with DJ Adam Owens from 95.3 DNH – complete with a champagne toast, dessert station and balloon drop at midnight! Grab your tickets and reserve a room today!

New Year’s Celebration

Monday thru Wednesday, December 29 thru January 1
Ring in 2020 at the Villa Roma Resort & Conference Center. Enjoy headline entertainment, a rocking New Year’s Eve party, live DJ, balloon release at midnight, a New Year’s Day brunch buffet and more.

Ugly Sweater & Happy New Year Party at Hector’s Inn

Wednesday, January 1 • 2-5pm
Make and wear your ugliest sweater for your chance to win a prize! Free jukebox, games, good friends, and lots of laughs.

New Year’s Meditation Retreat: The Power to Transform

Friday thru Sunday, January 3-5
The New Year represents a new beginning – an opportunity to reflect on the year gone by and come to conclusions about how best to spend the coming year. Join this beginner-friendly retreat at Kadampa Meditation Center. Discover timeless wisdom and practical methods for bringing about sustainable change and authentic happiness.

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