2021 Festivals & Fairs - Westport Moms
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2021 Festivals & Fairs


2021 International Festival of Arts & Ideas

May 14-June 27

A collection of events, groups, and activities ranging from everything from hair art to story telling!

2021 Robin Hoods Fair

May 22-June 20, Harwinton, CT

A Medieval festival featuring sword swallowers, jugglers, slack-rope walkers, high energy music, battling knights, and a REAL medieval joust!

2021 Westport Fine Arts Festival

May 29-30, Westport, CT

Come to downtown Westport to see works of art from all over!


2021 Middletown Pride

Virtual, June 5

Show your support for LGBT+ and enjoy live performances!

2021 South Windsor Strawberry Fest

June 12, South Windsor, CT

A festival to celebrate strawberries! eat strawberry shortcake, enter the Little Miss Strawberry Pagent, and more! and it’s free!

2021 Torrington Strawberry Festival

June 12, Torrington, CT

Enjoy a day filled with fun, shopping, food, and of course, delicious fresh-made Strawberry Shortcake!

2021 Monroe Congregational church Strawberry Festival

June 19-20, Monroe, CT

Another strawberry festival! enjoy strawberries and fun!

2021 Norwalk Art Festival

June 26-27, Norwalk, CT

Look at art from all over while enjoying live performances and a food court!


2021 Niantic Lions Art and Craft Show

July 3-4, Niantic, CT

New England’s finest artists and crafters displaying their creations of juried fine arts and crafts including paintings, photography, pottery, jewelry, woodworking and paper products, and it’s free!

2021 North Stonington Agricultural Fair

July 8-11, North Stonington, CT

Home Arts & Crafts, Commercial Vendors, Amusements, Livestock Shows, Motorized Sports, Games, Food and lots of family fun!


2021 Chabad of the Shorline Jewish Festival

August 1, Guilford, CT

2021 North Branford Potato and Corn Festival

August 5-8, North Branford, CT

2021 Lebanon Country Fair

August 6-8, Lebanon, CT

2021 Podunk Bluegrass Festival

August 12-15, Goshen, CT

2021 Mystic Outdoor Art Festival

August 14-15, Mystic, CT

2021 Bridgewater Country Fair

August 20-22, Bridgewater, CT

2021 Milford Oyster Festival

August 21, Milford, CT

2021 Brooklyn Fair

August 26-29, Brooklyn, CT

2021 Chester Fair 

August 27-29, Chester, CT

2021 Terryville Lions Country Fair

August 27-29, Terryville, CT


2021 Haddam Neck Fair

September 3-6, Haddam, CT

2021 Woodstock Fair

September 3-6, Woodstock, CT

2021 Greenwich Town Party Music Festival

September 4, Greenwich, CT

2021 Goshen Fair

September 4-6, Goshen, CT

2021 Connecticut Renaissance Faire

September 4-October 17, Lebanon, CT

2021 North Haven Fair

September 9-12, North Haven, CT

2021 Hebron Harvest Fair

September 9-12, Hebron, CT

2021 Wapping Fair

September 9-12, South Windsor, CT

2021 Simsbury Arts and Crafts Festival

September 10-11, Simsbury, CT

2021 Bethlehem Fair

September 10-12, Bethlehem, CT

2021 Norwalk Oyster Festival

September 10-12, Norwalk, CT

2021 LEVAS Gospel Festival and Fair

Virtual, September 11

2021 St. Peter’s Episcopal Church Apple Festival

September 11-12, Monroe, CT

2021 Suffield on the Green

September 11-12, Suffield, CT

2021 Glastonbury Arts on the Green Fine Art and Craft Show

September 11-12, Glastonbury, CT

2021 Four Town Fair

September 16-19, Somers, CT

2021 Guilford Fair

September 17-19, Guilford, CT

2021 Berlin Fair

September 17-19, Berlin, CT

2021 Newtown Arts Festival

September 17-19, Newtown, CT

2021 Hamden Fest 

September 18, Hamden, CT

2021 Seymour Pumpkin Festival

September 18, Seymour, CT

2021 Orange Country Fair

September 18-19, Orange, CT

2021 Durham Agricultural Fair

September 23-26, Durham, CT

2021 Guilford Performing Arts Festival

September 24-26, Guilford, CT


2021 Portland Agricultural Fair

October 1-3, Portland, CT

2021 Harwinton Fair

October 1-3, Harwinton, CT

2021 Old Saybrook Arts and Crafts Show

October 2-3, Old Saybrook, CT

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