Weekly Free Tastings at Vino!! Wine Shop
2025-08-22 17:00 - 19:00, 2025-08-29 17:00 - 19:00 (America/New_York) | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Weekly free tastings at Vino!! Wine Shop are hosted every Friday. Experts share their picks of wines with varied pricing and from diverse locations. Tasting details, including which wines will be served, are shared on their Facebook Page and in their newsletters.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Live Piano Music at The Sycamore
2025-08-22 18:00 - 21:00, 2025-08-23 18:00 - 21:00, 2025-08-26 18:00 - 21:00, 2025-08-28 18:00 - 21:00, 2025-08-29 18:00 - 21:00 | 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.

96.1 BBB Summer Jam Music Series at MOSAIC
2025-08-22 19:00 - 21:00 | Philip H. Kohl MOSAIC Family Commons, 457 Freedom Parkway, Pittsboro, NC, 27312, United States
Shag the night away at the 96.1 BBB Summer Jam Music Series at MOSAIC, powered by Brightspeed! Join MOSAIC at Chatham Park at the Tommy Edwards Stage for the ultimate beach music bash, courtesy of 96.1 BBB “Your Life. Your Music.” So grab your dancing shoes, join the shaggers on the dance floor, and dance like nobody’s watching! MOSAIC’s new dance floor is sponsored by the Sara Donaldson State Farm Insurance Agency.
The lawn opens at 6pm and the concert begins at 7pm. This event is FREE and open to the public, but registration is required. See the full schedule below and find your link to register:

Fri, Apr 18, 7pm-9pm Too Much Sylvia, Register.
Fri, May 2, 7pm-9pm The Entertainers, Register.
Fri, May 16, 7pm-9pm Band of Oz, Register.
Fri, May 30, 7pm-9pm Liquid Pleasure, Register.
Fri, Jun 13, 7pm-9pm The Castaways, Register.
Fri, Jun 27, 7pm-9pm The Embers, Register.
Fri, Aug 22, 7pm-9pm Back To School Bash: Chairmen of the Board, Register.

Anticipate bag checks and security screenings upon entry. Food or beverages purchased outside MOSAIC, weapons, and illegal substances are prohibited. Food and beverages will be available onsite for purchase – be prepared to present your receipt to event security. Bring a lawn chair or a blanket. Pets are welcome. This event is held outdoors on the Philip H. Kohl MOSAIC Family Commons. See more events hosted by MOSAIC at Chatham Park.

Come Out and Play Sculpture Show
2025-08-23 12:00 - 20:00, 2025-08-24 12:00 - 20:00 | JimGin Farm, 150 Wild Horse Run, Pittsboro, NC, 27312, United States
Dozens of artists, creating in a myriad of media, are represented in this annual Come Out and Play Sculpture Show, now in its 24th year. The event takes place on a 17-acre homestead and is a gift from hosts to guests and artists. Artists do not pay a participation fee and keep all proceeds from their sales (many of the works on display are for sale). There are some out-of-state artists, but most are local to North Carolina. Each reception is filled with fantastic art and local vendors, free food and drink from the artists and hosts, visits with the horses and pigs, and live music from the North Carolina Songwriters Co-op.
The opening reception for 2025 is Sat, Aug 23 and Sun, Aug 24, 12pm until dark. Additional receptions are hosted on the following Saturdays: Aug 30, Sep 6, Sep 13, and Sep 20, 12pm until dark. Events are free. This event is family-friendly and pet-friendly (please keep all dogs on a leash). For more information, contact Debbie Meyer at writetoeloise@gmail.com or 919.357.6142.
DIRECTIONS AND PARKING
Location: JimGin Farm, 150 Wild Horse Run, Pittsboro, NC, 27312.
Find Your Way With #w3w: ///lizard.exhausting.profuse.
Parking Directions: Come down Wild Horse Run to the end. Please do not park on this road. On the right-hand side, go through the wooden gates and park on the right lawn. In the event that the right lawn is full, folds will be there to guide you to parking on the left. There is plenty of parking, so please follow their guidance and do not block any roads going in or out.
ACCESSIBILITY INFORMATION
The farm is not paved but there are gravel and grass areas. Parts of the property can be navigated with care for those with walkers or wheelchairs, including the outdoor area where tents are set up and where the musicians perform. Many individuals with walkers and wheelchairs, including the artists themselves, attend the event every year. Please contact the event organizer for additional accessibility questions.

THE HISTORY BEHIND THE EVENT
The Come Out and Play Sculpture Show began in 2002 to commemorate the first anniversary of 9/11 and has continued since then to promote kindness in the world through art and by connecting people. Debbie Meyer and her husband, Eric Brantley, coordinate and host this amazing show each year; it is truly a rewarding gift!

Luxury Aged Sake Tasting in Celebration of Koshu's First Anniversary
2025-08-23 12:00 - 20:00, 2025-08-24 12:00 - 18:00 | Koshu Sake, 193 Lorax Lane, Unit 5, Pittsboro, NC, 27312, United States
Try some of the world’s finest sake and learn what makes it unique at this Luxury Aged Sake Tasting in Celebration of Koshu’s First Anniversary. Koshu means aged sake, and that’s what Koshu Sake Bar specializes in. Come in at your convenience during their regular hours, and they will guide you through the differences between each premium sake.
Tastings include 1-ounce pours of four different premium sake:

Born Dreams Come True Junmai Daiginjo is crafted from rice polished to 35% and aged for 5 years at a temperature of 23°F. Smooth and silky, with complexly layered flavors that include papaya, mango, rosewater, peach, and honey.
Dewazakura Yukimanman “Snow Country” Daiginjo is polished to 35% and aged for 5 years at 25°F. Well-rounded, full-bodied, and smooth, with persimmon and pomegranate notes.
Amabuki Rhododendron Junmai Daiginjo is polished to 40% and aged for 3 years at 32°F. Brewed with rhododendron yeast for a pleasant acidity, bold umami flavors, light floral undertones, and dry finish.
Born Gold Junmai Daiginjo is polished to 50% and aged for one year at 14°F. A mild floral sweetness carries hints of melon, pear, and refreshing citrus zest.

Tastings will be held on the following dates:

Fri, Aug 22, 2pm-8pm.
Sat, Aug 23, 12pm-8pm.
Sun, Aug 24, 12pm-6pm.

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. There is free parking. This event is FREE. Ages 21 and above are welcome. See all events at The Plant.

Tasting Classes with EB Wines
2025-08-23 14:00 - 15:00 | EB Wines, 40140 Moring, Chapel Hill, 27517, United States
The seventh annual Wine Tasting Classes is a collection of monthly wine tasting classes hosted by Esteban Brunello, owner of EB Wines. The classes are informative yet relaxed and open to guests with varying levels of knowledge, from novice wine drinkers to seasoned tasters. Classes are led by owner and wine director Esteban Brunello, who guides guests through the wine tasting process. Guests will learn to identify various wine notes, discover techniques in the winemaking process, and receive recommendations for food pairings.
Mark your calendars for the following class dates:

Sat, Jul 26, 2pm-3pm Refreshing Whites.
Sat, Aug 23, 2pm-3pm Skin Contact.
Sat, Sep 20, 2pm-3pm Domestic Wines.
Sat, Oct 18, 2pm-3pm Obscure Reds.
Sat, Nov 15, 2pm-3pm Fall Reds.
Sat, Dec 13, 2pm-3pm Sparking – Petillant Naturel.

EB Wines is part of the Chatham County Craft Beverages & Country Inns Trail. See all events at EB Wines.

Free Sake Tastings
2025-08-23 14:00 - 16:00 | Koshu Sake, 193 Lorax Lane, Unit 5, Pittsboro, NC, 27312, United States
Join Koshu Sake for Free Sake Tastings hosted on select weekends, April-October, 2pm-4pm. Sample new and unique sakes curated by their thoughtful team. Tastings will take place on the following dates:

Sat, Apr 19, 2pm-4pm The Hemparoo.
Sun, May 25, 2pm-4pm Strawberry Social.
Sat, Jun 14, 2pm-4pm Father’s Day Weekend.
Sat, Jul 19, 2pm-4pm.
Sat, Aug 23, 2pm-4pm: Koshu’s One-Year Anniversary. See details for Anniversary Luxury Sake Tasting.
Sat, Sep 27, 2pm-4pm MeadFest.
Sat, Oct 18, 2pm-4pm.

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. There is free parking. This event is FREE. Ages 21 and above are welcome. See all events at The Plant.

Live Music: Righteous Roots
2025-08-23 15:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Righteous Roots on Sat, Aug 23, 3pm-6pm. Righteous Roots is the songwriting and production of East Coast-based guitarist and vocalist Tom Leighton. They utilize modern electronic production techniques in combination with elements of rock and reggae to create a refreshingly unique studio sound coined ‘Island Rock’. Since its creation in 2021, Righteous Roots has performed hundreds of shows and dozens of festivals throughout VA, NC, MD, SC, PA, TN, WV, and DC.
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they are in a position of having to cancel, they will try to do so well in advance. 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 pets are allowed. This event is free! See all events at The Plant.

Live Music: Bella G
2025-08-23 18:00 - 21:00 | NC
Havoc Brewing Company presents Live Music with Bella G on Sat, Aug 23, 6pm-9pm. Captains Gastro food truck will be onsite at Havoc 5pm-9pm.
This event is free and takes place outdoors, weather permitting. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available onsite. Pets are welcome. This space is wheelchair accessible. More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Euchre Mondays at bmc
2025-08-25 18:00 - 20:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join a fantastic group of Euchre enthusiasts every Monday, 6pm-8pm, for Euchre Mondays. This weekly gathering is built around the classic trick-taking card game. No experience is needed — a fantastic regular euchre group is happy to bring newcomers up to speed, so you can show up solo or with friends and jump right in. Monday doubles as $5 pint night at bmc brewing, so you can pair your hand of cards with one of the 18 beers bmc brews on site, alongside hard cider, hard seltzer, wine, and non-alcoholic options.
The event is free and takes place indoors. The space is wheelchair accessible, and on-site parking is free. Pets are not permitted indoors at bmc brewing. bmc brewing is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

$10 Tuesday Tastings at Fair Game
2025-08-26 10:00 - 20:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Fair Game Beverage Company hosts $10 Tuesday Tastings every Tuesday, 10am-8pm. Come out on Tuesdays and enjoy a tasting of your choice of their housemade spirits, Whiskey, liquors, or NC beer/wine/cider flights.
This event takes place indoors. 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 pets are allowed but discouraged. See all events at The Plant.

Fearrington Farmers Market
2025-08-26 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.

Run Club at House of Hops
2025-08-26 18:00 - 20:00 | NC
Join House of Hops every Tuesday, 6pm-8pm for Run Club and 20%-off mixed six pack. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at Hops and Berry
2025-08-26 19:00 - 21:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come to Hops and Berry-Pittsboro for Music Bingo every Tuesday, 7pm-9pm. Instead of numbers, players listen for tracks and mark their cards as they recognize each tune, racing to fill a line before anyone else. It’s a low-key, high-energy way to spend a weeknight, and the format welcomes everyone from casual listeners to die-hard music buffs.
This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See more events at Hops & Berry. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Pub Trivia at Doherty's
2025-08-26 19:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for Pub Trivia every Tuesday, 7pm-9pm, hosted by Patrick W. Trivia. Trivia is free to play, with prizes for first, second, and third place.
See more events at Doherty’s.

Blues Jam at The MOD
2025-08-26 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 Tuesday, 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.

Music Bingo at House of Hops
2025-08-27 18:00 - 20:00 | NC
Join House of Hops every Wednesday, 6pm-8pm for Music Bingo hosted by DJ Special K. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Jazz Nights at The Sycamore
2025-08-27 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.

Acoustic Irish Music Seisiún
2025-08-27 18:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for an Acoustic Irish Music Seisiún on the last Wednesday of every month, 6pm-9pm. Whether you’re just beginning your music journey, a seasoned pro, or just love to listen, bring your instruments and passion for Irish music for an evening of lively tunes and great company. Musicians will be upstairs.
See more events at Doherty’s.

Karaoke at Hops and Berry
2025-08-27 19:00 - 22:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Karaoke every Wednesday, 7pm-10pm. The taproom’s weekly Karaoke night turns its live-entertainment stage over to the crowd, where regulars and first-timers alike line up to belt out their favorites—whether that’s a power ballad, a crowd-singalong anthem, or a deep cut only you remember. With a supportive, come-as-you-are vibe, it’s as fun to cheer from a table as it is to step up and perform.
This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See more events at Hops & Berry. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Run Club at Thirsty Skull PBO
2025-08-28 17:00 - 18:30 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Thirsty Skull Brewing – Pittsboro every Thursday, 5pm-6:30pm for Run Club.
See all events at Thirsty Skull Brewing – PBO. Part of the Chatham County Craft Beverages & Country Inns Trail.

Opinionation Trivia at House of Hops
2025-08-28 18:00 - 20:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops every Thursday, 6pm-8pm for Opinionation Trivia. This Family Fued-style trivia game is so much fun! Play at 6pm and again at 7pm for two chances to win $15 or $25 House of Hops gift cards. Bring the crew, bring food from neighbors Cafe Root Cellar or Mi Cancun, and enjoy!
More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Chef's Dinner at West End
2025-08-28 18:00 - 22:00 | West End Kitchen and Catering, Pittsboro, North Carolina, 27312, United States
Join West End each month for an exceptional Chef’s Dinner featuring five courses, including three options (vegetarian, pescatarian, and meat) for the main course, with optional wine pairings (announced before each event) selected by the in-house Sommelier. The first seating is at 6pm, and guests are welcome to arrive between 5:30pm-6pm. West End asks that you be done by 7:30pm to accommodate their second seating (guests are welcome to arrive between 8pm and 8:30pm). Upcoming dates are listed below:

Thu, Apr 24, 6pm-10pm April Chef’s Dinner.
Thu, May 15, 6pm-10pm May Chef’s Dinner.
Thu, Jun 19, 6pm-10pm June Chef’s Dinner.
Thu, Jul 24, 6pm-10pm July’s Chef’s Dinner.
Thu, Aug 28, 6pm-10pm August Chef’s Dinner.
Thu, Sep 25, 6pm-10pm September Chef’s Dinner.
Thu, Oct 23, 6pm-10pm October Chef’s Dinner.

See more events at West End Kitchen and Catering.
