Live Piano Music at The Sycamore
2025-12-20 18:00 - 21:00, 2025-12-23 18:00 - 21:00, 2025-12-25 18:00 - 21:00, 2025-12-26 18:00 - 21:00, 2025-12-27 18:00 - 21:00, 2025-12-30 18:00 - 21:00 (America/New_York) | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Tuesday, Thursday, Friday, and Saturday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Live Piano Music. The series features a rotating list of local musicians. Past and present musicians include Kris Whitenack, Robert Griffin, Lindsey Rosebrook, and Stephanie Schmitt. See the upcoming lineup here.
See more events at The Sycamore at Chatham Mills.

Live Music: Stone Dolls at Havoc
2025-12-20 18:00 - 21:00 | NC
Havoc Brewing Company presents Live Music with Stone Dolls on Sat, Dec 20, 6pm-9pm.
This event is free and will take place both indoors and outdoors, weather permitting. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available in the lot across the street. Pets are welcome. This space is wheelchair accessible. More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

The Graveyard Shift at The MOD
2025-12-20 20:00 - 23:59 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for The Graveyard Shift, a monthly dark disco dance party. All are welcome. This event is for ages 21+ and the cover is $5 per person. Upcoming event dates and guest DJs are listed below:

Sat, Jun 28, 8pm-12am Mouse the DJ.
Fri, Jul 18, 8pm-12am Guest DJ [SIN]APTIK.
Sat, Aug 16, 8pm-12am Guest DJ Ninjaficator.
Sat, Sep 13, 8pm-12am Guest DJ Baronovva.
Fri, Oct 31, 8pm-12am Guest DJ Lady Attercop.
Sat, Nov 22, 8pm-12am Mouse the DJ.
Sat, Dec 20, 8pm-12am Guest DJ That Darling DJ Duo.

See more events at The MOD.

Crafternoons at Clapping Hands Farm
2025-12-21 13:00 - 17:00, 2025-12-28 13:00 - 17:00 | Clapping Hands Farm, 3348 Alston Chapel Road, Pittsboro, NC, 27312, United States
Join Clapping Hands Farm for Crafternoons hosted every Sunday, December 2025-February 2026, 1pm5pm. This is a drop-in crafting circle, not a class. Bring a project you’re already working on, or join many of our crafters who are making items to donate to the Camp Store—a fun way to craft with purpose. You’re also welcome to come learn by doing; they’re happy to help folks get started, especially if it supports camp scholarships.
Classes usually take place at Clapping Hands Farm, unless otherwise posted, in their cozy, heated studio space. There is no fee to participate, but donations are welcome. Adults are welcome, and crafty teens may come solo. Children are welcome with a parent who can take full responsibility (the space is small and not ideal for toddlers). The camp store will be open during crafternoon sessions and by appointment through December and early January. All proceeds support camp scholarships. Come craft, connect, and help make camp accessible for more kids. Call 919.542.5599, email clappinghandsfarm@gmail.com, or send a WhatsApp message to RSVP. See more events at Clapping Hands Farm.

Donald Davis Annual Storytelling
2025-12-21 14:00 - 15:00 | Fearrington Barn, 500 Market Street, Pittsboro, NC, 27312, United States
Fearrington Village is delighted to welcome back their beloved friend and storyteller, Donald Davis, for their Annual Storytelling on Sat, Dec 20, 11am-12pm and Sun, Dec 21, 2pm-3pm. After a hiatus last year, their fundraiser for the Chatham food pantry, CORA, is back. And they will tell you, the holidays just don’t start at McIntyre’s until Donald arrives in Fearrington. Please bring canned goods and/or a monetary donation to support our Chatham food pantry. Purchase your tickets here.
Capacity for this event is extremely limited – they expect to sell out rapidly. A $10 ticket is required to attend. Children cannot get in for free due to limited space. Unlike Fearrington’s other events, the ticket price is not deductible from related Event Books and Tapes. All monies gathered from tickets will go directly to CORA. The most needed items for this month are cereal, oatmeal packets, cooking oil, soup, apples, and pasta sauce. Find more information about CORA’s needs and programs here.
See more events at Fearrington Village. Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail.

Winter Solstice Sound Bath Journey + Rose Tea Ceremony with Maia Rhenish
2025-12-21 16:00 - 18:00 | NC
Join Yoga Garden PBO for a Winter Solstice Sound Bath Journey + Rose Tea Ceremony with Maia Rhenish on Sun, Dec 21, 4pm-6pm. On the longest night of the year, come together to honor the winter season and the quiet light within. Join Maia Rhenish for a heart-centered gathering of sound and ceremony. The evening will begin with a rose tea meditation, opening your senses to the gentle, healing frequency of Rose. You’ll then flow into slow somatic movement and vocal toning, preparing the body and heart for an hour-long sound bath journey focused on the heart chakra. Bathed in Maia’s voice, gong, singing bowls, chimes, tuning forks, and drums, you’ll be guided into a space of inner peace and heartfelt connection. Together, embrace the darkness as a time to rest deep, reflect, and open to the returning light.
This class is $44 per person. Space is limited, so please preregister. See more events at Yoga Garden PBO.

Fearrington Farmers Market
2025-12-23 15:00 - 17:00, 2025-12-30 15:00 - 17:00 | Fearrington Farmers Market, E Camden, Pittsboro, NC, 27312, United States
The Fearrington Farmers Market is a producers-only market open Mar-Oct, Tuesdays, 4pm-6pm, and Nov-Feb, Tuesdays, 3pm-5pm, year-round in Fearrington Village. Bring reusable tote bags and plan to explore the many local vendors. You also might chat with the farmers, see old friends, or meet new ones! It’s a welcoming, inclusive, and friendly atmosphere that encourages healthy, happy living.
Fearrington Farmers Market has more than 3 dozen members and is now in its 30th season. Not all vendors are there every week, but some vendors are there every week, year-round. Each market features live music. Vendors include Celebrity Dairy, In Good Heart Farm, and bmc brewing. See their full list of vendors.
Come early if you’d like to review what is being offered; sales begin at the scheduled time, signaled by the bell. Bring along small bills ($20 or lower) to pay for your purchase. Some vendors accept credit and debit cards, and most will accept checks. This event takes place outdoors, rain or shine. Entry is free. Leashed, well-behaved pets are welcome. See more events at Fearrington Village.

Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill
2025-12-23 19:30 - 21:30 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join Fair Game Beverage Company in the Wheelhouse for Jennifer Curtis + Matthew Greenslade — A Special Holiday Double Bill on Tue, Dec 23, 7:30pm-9:30pm. Jennifer Curtis returns for another Wheelhouse show, accompanied by Matthew Greenslade with festive Christmas tunes—plus some special guests! Matthew Greenslade will bring the holiday spirit and perform music from The Real Christmas Book! This is a show you don’t want to miss!
Composer and performer Jennifer Curtis has been described as a “multi-genre maverick” by the San Diego Union-Tribune. Her second solo concert in Carnegie Hall was described by the New York Times as “one of the gutsiest and most individual recital programs,” and she was celebrated as “an artist of keen intelligence and taste, well worth watching out for.” As a violinist, Jennifer has won the Milka-Astral Grand Prize for Violin, the Juilliard Concerto Competition, and competed in Austria at the International Brahms Competition. You can read her full biography here.
This event takes place indoors in the Wheelhouse. Tickets are $30 per person plus a $0.75 ticket service fee. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Pets are not allowed. See all events at The Plant.

Jazz Nights at The Sycamore
2025-12-24 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Wednesday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Jazz Nights every Wednesday, 6pm-9pm. The series features a rotating list of local musicians. The Sycamore also offers their Lounge Menu in the dining room on Wednesday nights. Reservations are highly recommended. Past and present musicians include the Steve Hobbs Trio, Lauren Meehan, Dave Quick Jazz, and the Tony Galiani Jazz Quartet. See the upcoming lineup here.

Blues Jam at The MOD
2025-12-25 19:00 - 22:00, 2026-01-01 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Blues Jam hosted every Thursday, 7pm-10pm by Lo Taylor. This open jam is an excellent opportunity for those who share a love for the blues and wish to share their talents. Mr. Taylor and his band of talented musicians will make you feel right at home on our stage. Bring your voice, bring your instruments, or just bring your ears to partake in this musical delight. The Mod is dedicated to providing space for live music, great food, craft beverages, community, and love. Arrive early for musician sign-up or to grab a table for the evening. Any schedule changes due to weather, holidays, or unforeseen circumstances will be posted on their Facebook and Instagram pages.
See more events at The MOD.

Line Dancing Classes at Chatham Mills
2025-12-26 11:00 - 12:00 | Forest Hall at Chatham Mills, 480 Hillsboro Street, Suite 350, Pittsboro, NC, 27312, United States
Build your skills on the dance floor with Line Dancing Classes at Chatham Mills, hosted by Forest Hall at Chatham Mills and the Chatham Social Club every Friday, 11am-12pm. The cost is $25 per class, and all skill levels are welcome; no partner is needed for class. Register now at chathamsocialclub.com – limited spots available! See more events at Chatham Mills.

Run and Roam Fridays at The Plant
2025-12-26 17:00 - 21:00, 2026-01-02 17:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant after work and/or school for Run and Roam Fridays, hosted every Friday evening, Sep 5-Dec 12, 5pm-9pm. Come out for food and drink specials and plenty of family-friendly fun, including games, hula hoops, bubbles, chalk art, and more. Sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country Inns Trail, with local beers from bmc brewing, wines and ciders from Starrlight, spirits from Fair Game, and sake from Koshu. Local dining available at Kingston 99 Kitchen and Ta Contento.
This free event takes place indoors and outdoors. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. See all events at The Plant.

Live Music: Jason Damico
2025-12-27 19:30 - 22:30 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Live Music with Jason Damico. Performances take place on the following dates:

Sat, Jun 7, 7:30pm-10:30pm.
Sat, Aug 23, 7:30pm-10:30pm.
Sat, Oct 25, 7:30pm-10:30pm.
Sat, Dec 27, 7:30pm-10:30pm.

This event is free and takes place indoors. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Paint and Pint Night at House of Hops
2025-12-29 18:30 - 20:30 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops for a Paint and Pint Night on Mon, Dec 29, 6:30pm-8:30pm. Come cozy up at House of Hops while Wine & Design guides you through a step-by-step instructed paint class on pre-sketched canvases.
Tickets are $25 per person. No experience required. Arrive 30 minutes early to order your drinks! Wine & Design will have everything ready for you to create your very own masterpiece. The event is NOT BYOB; discounts and coupons are not valid. Email chapelhill@wineanddesign.com with any questions!!
This event takes place indoors. House of Hops is pet-friendly. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.
CANCELLATION POLICY
All sales are final; no refunds will be issued if a customer cancels their reservation. To receive a credit, the customer must email chapelhill@wineanddesign.com 24 hours before the event. Please note that if you book a reservation within 24 hours of the class, you will not receive a credit if you cannot attend. If there is a threat of inclement weather or the event has low attendance, it may be cancelled. If this is the case, you will be given credit for another class of equal value.

New Year's Eve Party at Doherty's
2025-12-31 16:30 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for an unforgettable New Year’s Eve Dinner and Party on Wed, Dec 31, 4:30pm-9pm. Get there early and enjoy any of their menu favorites, or indulge in Chef’s Specials for the evening (listed below). Plus, live music from Two Times Around starts at 6pm. There will be an Irish New Year Toast at 7pm EST (12am GMT). Come ring in the New Year with friends and family! Dinner reservations are available online.
CHEF’S SPECIALS

Smoked Pork Belly Bruschetta.
Prime Rib with a Merlot Demi-Glaze.
Lobster Pot Pie.
Sticky Toffee Pudding.

This event takes place indoors. Doherty’s first floor is wheelchair accessible and offers accessible seating. Free public parking is available just across the street. Leashed pets on the patio only, please. See more events at Doherty’s Irish Pub & Restaurant.

New Year's Eve Dinner at The Sycamore
2025-12-31 17:00 - 20:30 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Join The Sycamore at Chatham Mills for a New Year’s Eve Dinner on Wed, Dec 31, 5pm-8:30pm. They won’t be ringing in the new year, but they will have a beautifully curated Chef’s Tasting Menu ($110 per person, including one glass of champagne) designed to elevate your last evening of the year with rich flavors, seasonal inspiration, and elegant ambiance. With seatings available until 8:30pm, it’s the perfect way to savor a memorable, relaxed, and delicious final night of 2025. Reservations are filling quickly — secure your table now.
The menu for the evening is listed on The Sycamore’s website – click here for more details. The restaurant is ADA-compliant. Free parking is available in front of the restaurant. No pets allowed. See more events at Chatham Mills.

A Roving New Year's Eve!
2025-12-31 18:00 - 2026-01-01 00:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Welcome 2026 with A Roving New Year’s Eve at The Plant, Wed, Dec 31, 6pm-Thu, Jan 1, 12am. Join The Plant on New Year’s Eve for “one last crawl” to end 2025! Fair Game Beverage Company, bmc brewing, Starrlight Mead, and Koshu Sake will have festive beverages and creative spirit cocktails, specials, and, of course, sparkling wine by the bottle and glass. Kingston 99 Kitchen and Ta Contento will be open for dinner. There will be fire pits, an intention table, a dance party under the disco ball, and an hourly Apple Drop starting at 8pm and continuing until midnight to ring in 2026. Bring your friends and family- they’ve got something for everyone!
There is no cover fee for this free public event, and parking is free. Private tables and bottle service are available for a fee. Dress code is casual attire. The event takes place indoors and outdoors at The Plant. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Irish New Year at City Tap
2025-12-31 18:30 - 22:00 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
If you don’t like staying up until midnight, come celebrate an Irish New Year at City Tap on Wed, Dec 31, 6:30pm-10pm. The countdown will begin at 7pm EST (Dublin’s midnight). There will be live music from Trash Van Fever starting at 7pm as well! Enjoy a champagne toast and rocking tunes!
This event takes place at The City Tap. The patio is wheelchair-accessible from the back of the building. There is a lift to the second floor, and the service area is located on the secondary staircase that connects to the patio. See all events at City Tap.

Unisong: Guided Song Circle at NC Arts Incubator
2026-01-01 18:00 - 19:30 | NC Arts Incubator, 223 N Chatham Ave, Siler City, NC, 27344, United States
What medicine does your heart need? Join the NC Arts Incubator for Unisong: Guided Song Circle, hosted on the first Thursday of every month, 6pm-7:30pm. During this 90-minute journey designed for beginner and experienced singers alike, Unisong instructors will guide you through singing and movement that invite release, restoration, and healing of the heart.
See more events hosted by the NC Arts Incubator.

Winter Art Sale at the Vineyard
2026-01-02 11:00 - 17:00 | FireClay Cellars, 1276 Bowers Store Rd, Siler City, NC, 27344, United States
Join FireClay Cellars for a Winter Art Sale at the Vineyard. Winter is a little more inspiring! Browse an eclectic exhibition of fine art from the collections of Kate Ladd, Lucy Harris, and Wilma Schroeder while sipping a glass of wine. They’ll be open throughout the winter for the following hours:

Fridays, 11am-5pm.
Saturdays, 11am-5pm.
Sundays, 12pm-5pm.

Free parking is available on site. The porch and first floor are ADA-compliant, with wheelchair-accessible parking. FireClay Cellars is part of the Chatham County Craft Beverages and Country Inns Trail. Discover more events at FireClay Cellars.

Adult Begin to Sew Series with Checkered Tulip
2026-01-03 09:30 - 12:00 | Checkered Tulip, 35 West Chatham Street, Pittsboro, NC, 27312, United States
Join Checkered Tulip for this Adult Begin to Sew Series, hosted on select days throughout 2026. This workshop provides a structured introduction to essential sewing techniques for beginners or those looking to refresh their skills. Students will learn to safely operate a sewing machine and build a solid foundation for many years of happy sewing. Projects include: a tote bag, pillowcase, zippered pouch, apron, envelope pillow, and more. Single-day, two-week, and three-week sessions are offered. Upcoming classes include:

Sat, Jan 3 and 10, 9:30am-12pm: Two-Week Series; class projects include a pillowcase and apron. The cost is $115 per person.
Wed, Jan 14, 21, and 28, 6pm-8:30pm: Three-Week Series; class projects include a pillowcase, market tote, and zippered pouch. The cost is $175 per person.

At Checkered Tulip, you’ll be on a machine making your project from the get-go. Their instructors are there to help you bring your vision to life and give you one-on-one access to all the tricks and hacks that make your project a breeze. Students will be contacted concerning supplies following registration. Multi-part courses are hosted in consecutive weeks. This event takes place indoors. See more events at Checkered Tulip.
