FRIDAY
Rowan’s Autumn Stroll | Feather Hill Village, 53345 Main Road, Southold, 631-780-2851
From 5-8 p.m., Rowan Craft Boutique sponsors a stroll featuring vendors, pumpkin and face painting, raffles and music; free. For details, look here.
A Few Good Men | North Fork Community Theater, 12700 Old Sound Avenue, Mattituck, 631-298-4500
It’s opening night for this production of Aaron Sorkin’s courtroom drama at the NFCT. Shows run on Fridays and Saturdays at 7:30 p.m. and on Sundays at 2:30 p.m. for the next three weekends. Tickets are $18-33 and can be reserved here.
SATURDAY
World Migratory Bird Day | Bailie Beach Park, 751-1901 Bailie Beach Road, Mattituck, 631-298-9103
From 10 a.m. to noon, this event in conjunction with Turtleback Environmental Education Center teaches all ages how to help birds during migration, with a beach hike, raptor ID, crafts, puppets and more. Suggested fee is $20 per family; registration required here.
Think Pink Sip and Shop | J. McLaughlin, 54100 Main Road, Southold, 631-251-4735
From 1-4 p.m., 10% of sales will support local charity Kait’s Angels, with donations matched by Heidtmann & Sons Builders. Wine, charcuterie, desserts and raffles as well; free. For more info, click here.
Box Wine BBQ | Bridge Lane Wine, 35 Cox Neck Road, Mattituck, 631-298-1942
This annual event pops off from 5-8 p.m. with food from Maple Tree BBQ Smokehouse, sweets from The Treatery and live music. Tickets are $50 per person or $240 for a party box, which includes logo glasses, a box of wine and admission for four. To reserve, click here.
Sea Harvest Dinner | Maizeat at the Shoals Dockside, 61600 Main Road, Southold, 631-765-5121
Starting at 6 p.m., enjoy fish-based à la carte specials, Borghese rosé and fishmonger and cooking demos for the final dockside meal of the season. No tickets required; for details, look here.
SUNDAY
Car Show | Polo Grounds, 451 Moores Lane, Greenport
Greenport FD Relief Hose Company 2 hosts a car show from 9 a.m.-1:30 p.m. at the Greenport Polo Grounds, with food, music and raffles; free. For more info, click here.
Riverhead Country Fair | Downtown Riverhead
From 10 a.m.-5 p.m. visit this traditional country fair, with vendors, food and drinks, live music and judging of pies, cookies, jams and jellies, quilts, vegetables and more; free. For details, click here.
Oyster Fest | Greenport Harbor Brewing Company, 42155 Main Road, Peconic, 631-477-1100
Due to anticipated inclement weather, Oyster Fest will take place indoors at Greenport Harbor’s Peconic location from noon to 6 p.m. The annual event features local oyster farmers, food from Little Creek Oyster Farm & Market, a shucking contest, live music, vendors, and educational info; free. For details, look here.
Borromeo String Quartet | Shelter Island Presbyterian Church, 32 North Ferry Road, Shelter Island, 631-749-0805
Shelter Island Friends of Music presents its final concert of the 2025 season at 6 p.m. with a reception to follow. Free; donations accepted. For information, look here.
