Live Music & Events

summer seafood festival

Summertime Seafood Festival

Join us in downtown Pittsboro for the Summertime Seafood Festival, hosted by The Sycamore. Celebrate summer and seafood with delicious food, refreshing drinks, and live music by The Castaways. The event will be held on the back lawn, and inside of Forest Hall at Chatham Mills. Get your advance tickets for $10 or purchase at the door for $15 (if not sold out).


We will have a variety of chef-prepared, mouthwatering seafood (and non-seafood) options available for purchase, including Lobster Rolls, Oyster Po’Boys, Crabcake Sliders, Chilled Shrimp Cocktail, Carolina Style BBQ Spare Ribs, Tomato Sandwich, Smoked Fish Salad,  Watermelon, Grilled Shishito Peppers, Steamed Corn on the Cob, and more.


Quench your thirst with beer, wine, and summery cocktails from the cash bar.


Children under 12 enter for free, but please leave your furry friends at home. Doors open at 2pm, with music by The Castaways starting at 3pm. Lawn games and activities will be available for added enjoyment. Seating will be provided inside and out, but folding chairs and blankets are also welcome.


Space is limited, so secure your advance tickets today. Rain or shine, the festival will proceed with indoor accommodations if needed.


Please note your ticket is for entry and band cover. Food and Drinks are available for purchase.

Jazz Night Wednesdays

Jazz Night Wednesdays  

Every Wednesday night we feature Live Jazz from a series of rotating musicians, and we also offer the Lounge Menu in the Dining Room (Wednesdays only, along with full dinner menu).  Reservations highly recommended.  See schedule below for upcoming dates:

View Upcoming Dates

6/26 – Dave Quick Jazz

7/3 – Closed

7/10 – Steve Hobbs Trio

$10 lounge menu thursdays

$10 Lounge Menu Thursdays  

Join us every Thursday in the lounge and enjoy most of our plates for just $10.  The lounge features comfortable and cozy seating, a flat screen TV, pool table, and board games. 

$10 lounge menu thursdays

Live Piano Music

Dine to the relaxing ambiance of live piano music.  We feature various performers in our dining room on Tuesday, and Thursday-Saturday. (Wednesdays is Live Jazz).  Current performers include:

Kris Whitenack

Robert Griffin

Lindsey Rosebrook

Stephanie Schmitt