Discover Winthrop.com

January

Community Awards Night
The Winthrop Chamber of Commerce annual Kick-Off Dinner honors community leaders and volunteers during the social event of the year. Hyatt Harborside, Logan Airport 617-846-9898

March

Chili & Chowder Fest
Both restaurants and individuals enter their best chili or chowder for judging, with awards presented to the favorites. This event is a fundraiser for the Winthrop Art Association, with a $5 admission charge. Winthrop Senior Center, 35 Harvard Street 617-846-2644

April

Spring Art Festival
Winthrop Art Association exhibit featuring local artists and including craft tables and demonstrations by artisans. Takes place the last weekend of April. Admission is free. Winthrop Senior Center, 35 Harvard Street 617-846-2644

$10,000 Raffle & Silent Auction
The Winthrop Chamber of Commerce annual fundraiser features a raffle for the grand prize of $10,000 plus a Silent Auction featuring many great prizes. Cottage Park Yacht Club, 1 Baker Square 617-846-9898

May

Springtime Sidewalk Sale
Lots of bargains are to be found during the annual sales event all over Winthrop. There are also kids activities that day with arts and crafts in French Square. Held the weekend before Memorial Day. Winthrop Chamber of Commerce 617-846-9898

June

Strawberry Festival
The Winthrop Improvement and Historical Association holds this popular event at the Deane Winthrop House. All-you-can-eat strawberry shortcake. Tickets must be purchased in advance. Deane Winthrop House, 40 Shirley Street 617-846-8606

Hot Dog Safari
Eat all the hot dogs, sausages and ice cream you can, plus watch horse races all day at the famous Suffolk Downs racetrack. Proceeds benefit the Cystic Fibrosis Foundation. Suffolk Downs, East Boston 617-567-3900

Sandcastle Festival
Parks & Recreation sponsors the popular sandcastle contest at Yirrell Beach the last Saturday in June. There are many games and activities for kids of all ages. There is a $10 entry fee for the sandcastle competition. Yirrell Beach, Shirley Street 617-846-8243

July

Town Bonfire
As part of Winthrop’s Independence Day celebrations, there is a huge bonfire on Yirrell Beach July 3rd. The fire is lit at sunset and has become a favorite tradition. Yirrell Beach, Shirley Street 617-846-9898

4th of July Fireworks & Horribles Parade
Winthrop’s annual Horribles Parade, featuring homemade floats and kids and adults dressed in costume, departs from the Public Landing at 9:00 am ending up at Coughlin Park for field games. At 9:30 pm on the 4th of July, a large fireworks display takes place over Winthrop Harbor. Public Landing, Shirley Street 617-846-9898

Old Fashioned Family Day at the Beach
The Winthrop Chamber of Commerce sponsors this annual event the third Sunday in July. Held at Yirrell Beach on Point Shirley, there is plenty of free parking at the nearby Public Landing. There are many games and activities for kids of all ages, such as a moon-bounce, a hula-hoop contest, a giant slide, a hat contest, and a horseshoe tournament for adults. Yirrell Beach, Shirley Street 617-846-9898

East Boston Italia Unita Festival
This three-day Italian festival is held every third week in July as a celebration of the Italian culture. Central Square is transformed into an Italian "piazza-style" setting where people capture the essence of community and a feeling of unity. Thousands flock to sample authentic Italian cooking while enjoying the free entertainment and attractions. Central Square, East Boston 617-569-5000

Summer Concert Series
Parks & Recreation sponsors a family concert series under the gazebo in Ingleside Park on Wednesday nights in the summer. Ingleside Park, Walden Street 617-846-8243

August

Sunset Cruise on Boston Harbor
The Winthrop Chamber of Commerce sponsors an annual Boston Harbor sunset cruise in early August. The cruise departs from Deer Island where there is ample free parking. Boarding starts at 6:30 pm and tickets must be purchased in advance. MWRA Treatment Plant, Deer Island 617-846-9898

Five Sisters Swim
Swimmers of all types take part in the annual 1.2 mile swim around the breakers along Winthrop Beach, known as the “five sisters”. Winthrop Beach, Winthrop Shore Drive 617-846-9898

Make-A-Wish Regatta
Sailors compete in this exciting race while raising money for the Make-A-Wish Foundation. Cottage Park Yacht Club hosts this regatta the first weekend of August. Cottage Park Yacht Club, 1 Baker Square 617-846-2792

September

Taste of Winthrop
The Winthrop Chamber of Commerce puts on a night for sampling all the best restaurants the area has to offer. Held at the Winthrop Yacht Club with ample free parking, tickets are $30 per person. Winthrop Yacht Club, 649 Shirley Street 617-846-9898

October

Fall Fair & Craft Show
Parks & Recreation sponsors this annual event at Ingleside Park. There is pumpkin-painting, rides, food, and lots of tables featuring arts and crafts. Fun for the whole family. Ingleside Park, Walden Street 617-846-8243

Halloween Haunt
Kids in costume descend upon Winthrop Center every Halloween to trick-or-treat at over 50 businesses in a fun and safe environment. The route starts at the Winthrop Federal Credit Union at 4:00 pm. Winthrop Federal Credit Union, 15 Woodside Ave. 617-846-1226

November

Holiday Tree Lighting Festival
The day after Thanksgiving features many fun events, including live entertainment, ice sculptures, costumed characters, giveaways, raffles and free photos with Santa. The annual festival takes place from 3:00 – 6:00 pm with the highlight being Santa arriving on a fire truck to turn on the lights. French Square, Winthrop Center 617-846-9898

December

Santa’s Visit
Every Christmas Eve, Santa Claus makes his way through the town aboard a fire truck blaring carols. Kids rush out to wave and catch a glimpse of St. Nick on his route.

Go to the Community Calendar