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Jamesport Fire Department bazaar

Jamesport Washington Ave to Main Road, Jamesport, NY, United States

The Jamesport Fire Department’s annual bazaar runs July 14-18, with a parade Wednesday and fireworks Saturday night.

Jamesport Fire Department bazaar

Jamesport Washington Ave to Main Road, Jamesport, NY, United States

The Jamesport Fire Department’s annual bazaar runs July 14-18, with a parade Wednesday and fireworks Saturday night.

Jamesport Fire Department parade

Jamesport Washington Ave to Main Road, Jamesport, NY, United States

The Jamesport Fire Department's annual parade takes place on Main Road Wednesday, July 15, stepping off at 7 p.m.

Jamesport Fire Department bazaar

Jamesport Washington Ave to Main Road, Jamesport, NY, United States

The Jamesport Fire Department’s annual bazaar runs July 14-18, with a parade Wednesday and fireworks Saturday night.

Jamesport Fire Department bazaar

Jamesport Washington Ave to Main Road, Jamesport, NY, United States

The Jamesport Fire Department’s annual bazaar runs July 14-18, with a parade Wednesday and fireworks Saturday night.

Jamesport Fire Department bazaar

Jamesport Washington Ave to Main Road, Jamesport, NY, United States

The Jamesport Fire Department’s annual bazaar runs July 14-18, with a parade Wednesday and fireworks Saturday night.

Rev Up for Rise: Horsepower & Heart 2026 car show

Stotzky Memorial Park Riverhead, NY 11901

Rise Life Services will host “Rev Up for Rise: Horsepower & Heart 2026,” a community car show at Stotzky Park in Riverhead. The show runs 11 a.m. to 4 p.m. with free spectator admission, $20 car registration and donations encouraged; proceeds support fire door installation in Rise residential services.

Riverhead cardboard boat race

Peconic Riverfront Park Peconic Avenue, Riverhead, NY, United States

The Riverhead Cardboard Boat Race returns to the Peconic Riverfront with teams racing homemade cardboard boats across the Peconic River. The free event also includes a Family Fun Zone, vendor marketplace, kids’ games, food and entertainment, with the race start scheduled for 11 a.m.

Rev Up for Rise: Horsepower & Heart 2026 car show

Stotzky Memorial Park Riverhead, NY 11901

Rise Life Services will host “Rev Up for Rise: Horsepower & Heart 2026,” a community car show at Stotzky Park in Riverhead. The show runs 11 a.m. to 4 p.m. with free spectator admission, $20 car registration and donations encouraged; proceeds support fire door installation in Rise residential services.

Riverhead’s Alive on 25 summer block party

Downtown Riverhead Main Street Downtown Riverhead - Main Street, Riverhead, NY, US

Alive on 25 brings a summer block party to Main Street in downtown Riverhead with live music on multiple stages, craft beverages, food trucks and street vendors. The event also includes car shows and pro wrestling. Free admission.

Polish Town Fair

Polish Town USA Pulaski Street, Riverhead

The Polish Town Civic Association will host the 2026 Polish Town Fair on Saturday, Aug. 15 and Sunday, Aug. 16 in Riverhead’s Polish Town.

Hallockville Hootenanny

Hallockville Museum Farm 6038 Sound Avenue, Riverhead., NY

Hallockville Museum Farm hosts its first Hallockville Hootenanny with live music from five local bands, plus local food, vendors and family-friendly activities. Bring a lawn chair or blanket and spend the afternoon on the grounds by Naugles Barn.

Polish Town Fair

Polish Town USA Pulaski Street, Riverhead

The Polish Town Civic Association will host the 2026 Polish Town Fair on Saturday, Aug. 15 and Sunday, Aug. 16 in Riverhead’s Polish Town.

12th annual Southold American Legion car show

Southold American Legion Post 803 51655 Route 25, Southold, NY, United States

The Southold American Legion Post 803 hosts its 12th annual car show with antiques, hot rods, sports cars and motorcycles on display. The event includes live music by the New York Vendettas, the Meats Meat food truck, a raffle and a membership drive. Spectator admission is free; exhibitor vehicles pay $20.

Alive on 25

Downtown Riverhead East Main Street, Riverhead

The 2026 season finale of the Alive on 25 street festival is scheduled to take place on Sept. 10 in downtown Riverhead. The event offers live music, vendors, family friendly activities and more along Main Street. Admission is free Rain date: Sept. 25.

Greenport maritime festival

Mitchell Park Mitchell Park, Greenport, NY, US

The Greenport Maritime Festival is a village-wide celebration of maritime culture on Greenport’s working waterfront, with programming across Mitchell Park, the marina and surrounding streets. Southampton Animal Shelter Foundation will be on site Saturday with adoptable pets.

Wading River-Shoreham Chamber of Commerce fall festival

Shoppes at East Wind 5768 Route 25A, Wading River, NY, United States

The Wading River Shoreham Chamber of Commerce’s annual Fall Festival returns to The Shoppes at East Wind with live music by SouthBound, line dancing, food trucks, and local vendors. Kids’ activities include a bounce house, crafts, and hands-on activities. Free admission; rain or shine.

Country fair at Hallockville Museum Farm

Hallockville Museum Farm 6038 Sound Avenue, Riverhead., NY

Hallockville Museum Farm’s 45th annual Country Fair returns Oct. 3-4 with farm animals, tractors, craft demonstrations and vendors, children’s activities, wagon and kiddie train rides, tractor pulls, live music and food. Half-price admission is offered Sunday from 10 a.m. to noon.

Country fair at Hallockville Museum Farm

Hallockville Museum Farm 6038 Sound Avenue, Riverhead., NY

Hallockville Museum Farm’s 45th annual Country Fair returns Oct. 3-4 with farm animals, tractors, craft demonstrations and vendors, children’s activities, wagon and kiddie train rides, tractor pulls, live music and food. Half-price admission is offered Sunday from 10 a.m. to noon.

Wading River-Shoreham Chamber of Commerce fall festival

Shoppes at East Wind 5768 Route 25A, Wading River, NY, United States

The Wading River-Shoreham Chamber of Commerce hosts its annual Fall Festival on Sunday, Oct. 18 at The Shoppes at East Wind. The free, rain-or-shine event includes live music by SouthBound, line dancing, food trucks, vendors, and kids’ activities.

East End LOCAL