Connecticut’s Country Fairs and Festivals 2021

Country Fairs and Festivals throughout the state of Connecticut will be open this year!  These fairs are filled with entertainment, live music, carnival rides, animal exhibits and of course, delicious food.  There is always something for everyone! 

Wolcott Country Fair

August 20-22,2021 Wolcott Fairgrounds 245 Wolcott Road Wolcott, CT

Starting in 1979, the Wolcott Country Fair is the area’s largest agricultural and family fun event of the summer.

We’re back!!!! We’re proud to announce that we’ll be hosting our fair this year from August 20 – 22. Stay tuned for more updates!!!

We’re excited to announce that we have a new ride vendor (Rainbow Amusements). This means new and updated rides for all ages!!!!

Entertainment
We have a great line up of bands this year. Check out our Entertainment Page for further information. Also checkout out the Fair Schedule page for a full schedule of events.

Arena
We have a developed whole new area called The Arena featuring horse shows, barrel racing and more. Check out our new Arena Page for further information. Please check back for any updates.

Riverfront Asian Festival

August 21, 2021 Mortensen Riverfront Plaza, 300 Columbus Blvd. Hartford, CT 11am -4pm

Celebrate Asian and Pacific Island cultures through traditional music and dance, hands-on arts activities, food, and martial arts.

Dutchess County Fair

August 24- August 29    Dutchess County Fairgrounds on Route 9 in Rhinebeck, NY

This fair is the second largest fair in New York State. The 6-day Dutchess County Fair will feature Agriculture, Horticulture, Turn-of-the-Century Treasures, Working Blacksmith Shop & Gas Powered Engine Show, and so much more…

Brooklyn Fair

August 26 – 29, 2021 Brooklyn Fairgrounds Rte. 169 & 15 Fairgrounds Rd. Brooklyn, CT

Being the oldest continuously active agricultural fair in the United States, the Brooklyn Fair is pack full of fun with draft horses, livestock shows, home and garden exhibits, live entertainment, historical displays, special daily events, carnival rides, midway and great food.

Chester Fair

August 27-29, 2021     Kirtland Terrace, off Route 154 Chester, CT

This agricultural family fair features animal exhibits and competitions, a magic show, and fun for kids like frog jumping, reptile ponds, giant bubbles, balloon animals, and a bird presentation! Featuring plenty of interaction with and observation of animals, as well as a full midway with amusement rides.

Terryville Lions Club Fair

August 27-29, 2021 Terryville Fairgrounds 171 Town Hill Rd. Plymouth, CT

Founded in 1948, the Terryville Lions Country Fair is the biggest fundraiser of the year for the Terryville Lions Club. This year, the Terryville Fair few new surprises, like ATV and dirt bike drag racing, Jeep and pickup truck tug-of-war competitions and side-by-side truck racing. As well as great food, games and entertainment. 

Haddam Neck Fair

September 3-6, 2021 Haddam Neck Fairgrounds 26 Quarry Hill Rd. Haddam Neck, CT 

Haddam Neck Fair have been rated one of Connecticut’s major agricultural fairs and continues to operate successfully due in large part to the many volunteers whose hard  work maintains its agricultural tradition.. This fair is known for its family-friendly atmosphere and beautiful environment.

Woodstock Fair

September 2 – 3, 2021 Woodstock Fairgrounds 281 Rte. 169 South Woodstock, CT


Woodstock Fair is the state’s second oldest agricultural fair featuring tasty food, livestock shows, a petting zoo, free stage shows, a midway, go-kart races, strolling entertainers, plenty of vegetables and flowers, and much more.

Connecticut Rennaissance Fair 2021

September 4 – October 17, 2021  • 10:30am – 6pm Every Saturday & Sunday, Plus Labor Day and Columbus Day Monday
Lebanon Fairgrounds, 122 Mack Road Lebanon, CT

Enjoy a Medieval Marketplace, ancient music, traditional dances, birds of prey in flight, archery, a kingly feast. Costumes encouraged but not required. Come as you are or as you wish to be. Pets allowed. Dogs must have proof of rabies vaccination for entry.

Hebron Harvest Fair

September 9-12, 2021 Hebron Lion’s Fairgrounds 347 Gilead St. (Rte. 85) Hebron, CT

The Hebron Harvest Fair features a midway, entertainment, arts and crafts, food and product booths, small animal barns, animal shows and competitions and much more.

North Haven Fair

September 9-12, 2021 North Haven Fairgrounds 290 Washington Ave. (Rte. 5) North Haven, CT

Every year the North Haven Fair presents some of the greatest farm animals, baking and entertainment in the state; including exhibit buildings and booths, Old McDonald’s farm, live entertainment, good food, tractor pull and more.

Wapping Fair

September 9-12, 2021 South Windsor Fair Grounds 75 Brookfield Street South Windsor, CT

The Wapping Fair features livestock, rides, bands, magic, food truck festival, exhibits, children’s attractions, exotic animal meet and greet, vendors and more.

Bethlehem Fair

September 10-12, 2021 384 Main St North Bethlehem, CT

Old-fashioned agricultural fair with livestock, agricultural exhibits, horse show, horse drawing, art and photography show, farm displays, amusement rides, food, and entertainment.  This fair includes livestock, agricultural exhibits, horse show, horse drawing, Antique Tractor Pully, farm displays, amusement rides, food, and entertainment.

Four Town Fair

September 16-19, 2021   Four Town Fair Fairgrounds 56 Egypt Rd. (off Rte. 83) Somers, CT

The Four Town Fair has been going on over 178 years. We have a little something for everyone! There is live stage entertainment, pie eating & corn contest, animal pulls, doodle bug pulls, agricultural exhibits, crafts, plenty of food to please everyone and much more. Car Show on Thursday! Parade on Saturday morning 10:00 am starting Main St, Somers CT to the fair grounds. Admission is $6 on Thursday, $10 Friday, Saturday & Sunday. Children 12 and under FREE

Berlin Fair

September 17-19, 2021    Berlin Fairgrounds 430 Beckley Rd. Berlin, CT

This fair includes thrilling rides or just relaxing and watching a concert as well frog jumping and turtle racing. The packed schedule includes pie-eating contests, large animal and crafts exhibits and live entertainment throughout the weekend. This fair is for all ages!

The Big E

September 17-October 3, 2021  1305 Memorial Ave, West Springfield, MA 01089

The Big E, formally known as The Eastern States Exposition, is billed as “New England’s Great State fair”. It is the largest agricultural event on the eastern seaboard and the sixth-largest fair in the nation. Each September, more than 1.6 million people travel to Eastern States Exposition’s grounds for New England’s grandest fair – The Big E. The 17-day event provides a one of a kind tactile experience in which visitors can celebrate the season and to enjoy the sights, sounds and flavors of the region.

Guilford Fair

September 17-19, 2021 Guilford Fairgrounds Lovers Lane Guilford, CT


One of the oldest agricultural fairs in Connecticut when started as a Cattle Show in the fall of 1859.  The Guilford Fair offers live bands, midway rides, games and food, Cattle, Poultry, Sheep & Goats, Vegetables, Baking, Canning, Flowers, Arts & Craft, Needlework and Photography exhibits.

Orange Country Fair

September 18-19, 2021 Orange Fairgrounds 525 Orange Center Rd. (Rte. 152) Orange, CT

Features craft exhibits, antique cars, tractor pulls, pig racing, birds of prey, children’s games, country music, contests, flower and vegetable exhibits, critter and music shows, and much more.

Durham Fair

September 23-26, 2021 Main Street and Fowler Avenue Durham, CT

Filled with rides and games, tractor pulls, three livestock barns, crafts, exhibits featuring baking, canning, photography and horticulture, and a wide selection of fair food, the Durham Fair is Connecticut’s largest agricultural fair. This year there will also be a Demolition Derby, tractor pull, live music/shows, and fireworks and laser lights shows.

Harwinton Fair

October 1-3, 2021 Harwinton Fairgrounds 150 Locust Rd. Harwinton, CT


Harwinton Fair, originally known as Harwinton Cattle Show and Fair, is the yearly event of the Harwinton Agricultural Society. There will be Pig Races, Antique Tractor Show, Rabbit Costume Contest, Oxen Draw and Civil War Displays. Enjoy a magic show and bluegrass music after visiting the barnyard animals. Don’t forget to stop by the Country Store.

Portland Fair

October 1-3, 2021 Exchange Club Fairgrounds Rte. 17A Portland, CT

Livestock Shows, Bands, Truck & Tractor Pulls, Mug Bog, Live Music, Fair Food, Midway Rides, Ground Entertainment, Vendors, heated entertainment, beer & wine Tent, and much more!

Connecticut’s Country Fairs and Festivals 2021

Country Fairs and Festivals throughout the state of Connecticut will be open this year!  These fairs are filled with entertainment, live music, carnival rides, animal exhibits and of course, delicious food.  There is always something for everyone! 

Wolcott Country Fair

August 20-22,2021 Wolcott Fairgrounds 245 Wolcott Road Wolcott, CT

Starting in 1979, the Wolcott Country Fair is the area’s largest agricultural and family fun event of the summer.

We’re back!!!! We’re proud to announce that we’ll be hosting our fair this year from August 20 – 22. Stay tuned for more updates!!!

We’re excited to announce that we have a new ride vendor (Rainbow Amusements). This means new and updated rides for all ages!!!!

Entertainment
We have a great line up of bands this year. Check out our Entertainment Page for further information. Also checkout out the Fair Schedule page for a full schedule of events.

Arena
We have a developed whole new area called The Arena featuring horse shows, barrel racing and more. Check out our new Arena Page for further information. Please check back for any updates.

Riverfront Asian Festival

August 21, 2021 Mortensen Riverfront Plaza, 300 Columbus Blvd. Hartford, CT 11am -4pm

Celebrate Asian and Pacific Island cultures through traditional music and dance, hands-on arts activities, food, and martial arts.

Dutchess County Fair

August 24- August 29    Dutchess County Fairgrounds on Route 9 in Rhinebeck, NY

This fair is the second largest fair in New York State. The 6-day Dutchess County Fair will feature Agriculture, Horticulture, Turn-of-the-Century Treasures, Working Blacksmith Shop & Gas Powered Engine Show, and so much more…

Brooklyn Fair

August 26 – 29, 2021 Brooklyn Fairgrounds Rte. 169 & 15 Fairgrounds Rd. Brooklyn, CT

Being the oldest continuously active agricultural fair in the United States, the Brooklyn Fair is pack full of fun with draft horses, livestock shows, home and garden exhibits, live entertainment, historical displays, special daily events, carnival rides, midway and great food.

Chester Fair

August 27-29, 2021     Kirtland Terrace, off Route 154 Chester, CT

This agricultural family fair features animal exhibits and competitions, a magic show, and fun for kids like frog jumping, reptile ponds, giant bubbles, balloon animals, and a bird presentation! Featuring plenty of interaction with and observation of animals, as well as a full midway with amusement rides.

Terryville Lions Club Fair

August 27-29, 2021 Terryville Fairgrounds 171 Town Hill Rd. Plymouth, CT

Founded in 1948, the Terryville Lions Country Fair is the biggest fundraiser of the year for the Terryville Lions Club. This year, the Terryville Fair few new surprises, like ATV and dirt bike drag racing, Jeep and pickup truck tug-of-war competitions and side-by-side truck racing. As well as great food, games and entertainment. 

Haddam Neck Fair

September 3-6, 2021 Haddam Neck Fairgrounds 26 Quarry Hill Rd. Haddam Neck, CT 

Haddam Neck Fair have been rated one of Connecticut's major agricultural fairs and continues to operate successfully due in large part to the many volunteers whose hard  work maintains its agricultural tradition.. This fair is known for its family-friendly atmosphere and beautiful environment.

Woodstock Fair

September 2 - 3, 2021 Woodstock Fairgrounds 281 Rte. 169 South Woodstock, CT


Woodstock Fair is the state's second oldest agricultural fair featuring tasty food, livestock shows, a petting zoo, free stage shows, a midway, go-kart races, strolling entertainers, plenty of vegetables and flowers, and much more.

Connecticut Rennaissance Fair 2021

September 4 – October 17, 2021  • 10:30am – 6pm Every Saturday & Sunday, Plus Labor Day and Columbus Day Monday
Lebanon Fairgrounds, 122 Mack Road Lebanon, CT

Enjoy a Medieval Marketplace, ancient music, traditional dances, birds of prey in flight, archery, a kingly feast. Costumes encouraged but not required. Come as you are or as you wish to be. Pets allowed. Dogs must have proof of rabies vaccination for entry.

Hebron Harvest Fair

September 9-12, 2021 Hebron Lion's Fairgrounds 347 Gilead St. (Rte. 85) Hebron, CT

The Hebron Harvest Fair features a midway, entertainment, arts and crafts, food and product booths, small animal barns, animal shows and competitions and much more.

North Haven Fair

September 9-12, 2021 North Haven Fairgrounds 290 Washington Ave. (Rte. 5) North Haven, CT

Every year the North Haven Fair presents some of the greatest farm animals, baking and entertainment in the state; including exhibit buildings and booths, Old McDonald's farm, live entertainment, good food, tractor pull and more.

Wapping Fair

September 9-12, 2021 South Windsor Fair Grounds 75 Brookfield Street South Windsor, CT

The Wapping Fair features livestock, rides, bands, magic, food truck festival, exhibits, children's attractions, exotic animal meet and greet, vendors and more.

Bethlehem Fair

September 10-12, 2021 384 Main St North Bethlehem, CT

Old-fashioned agricultural fair with livestock, agricultural exhibits, horse show, horse drawing, art and photography show, farm displays, amusement rides, food, and entertainment.  This fair includes livestock, agricultural exhibits, horse show, horse drawing, Antique Tractor Pully, farm displays, amusement rides, food, and entertainment.

Four Town Fair

September 16-19, 2021   Four Town Fair Fairgrounds 56 Egypt Rd. (off Rte. 83) Somers, CT

The Four Town Fair has been going on over 178 years. We have a little something for everyone! There is live stage entertainment, pie eating & corn contest, animal pulls, doodle bug pulls, agricultural exhibits, crafts, plenty of food to please everyone and much more. Car Show on Thursday! Parade on Saturday morning 10:00 am starting Main St, Somers CT to the fair grounds. Admission is $6 on Thursday, $10 Friday, Saturday & Sunday. Children 12 and under FREE

Berlin Fair

September 17-19, 2021    Berlin Fairgrounds 430 Beckley Rd. Berlin, CT

This fair includes thrilling rides or just relaxing and watching a concert as well frog jumping and turtle racing. The packed schedule includes pie-eating contests, large animal and crafts exhibits and live entertainment throughout the weekend. This fair is for all ages!

The Big E

September 17-October 3, 2021  1305 Memorial Ave, West Springfield, MA 01089

The Big E, formally known as The Eastern States Exposition, is billed as "New England's Great State fair". It is the largest agricultural event on the eastern seaboard and the sixth-largest fair in the nation. Each September, more than 1.6 million people travel to Eastern States Exposition’s grounds for New England’s grandest fair – The Big E. The 17-day event provides a one of a kind tactile experience in which visitors can celebrate the season and to enjoy the sights, sounds and flavors of the region.

Guilford Fair

September 17-19, 2021 Guilford Fairgrounds Lovers Lane Guilford, CT


One of the oldest agricultural fairs in Connecticut when started as a Cattle Show in the fall of 1859.  The Guilford Fair offers live bands, midway rides, games and food, Cattle, Poultry, Sheep & Goats, Vegetables, Baking, Canning, Flowers, Arts & Craft, Needlework and Photography exhibits.

Orange Country Fair

September 18-19, 2021 Orange Fairgrounds 525 Orange Center Rd. (Rte. 152) Orange, CT

Features craft exhibits, antique cars, tractor pulls, pig racing, birds of prey, children's games, country music, contests, flower and vegetable exhibits, critter and music shows, and much more.

Durham Fair

September 23-26, 2021 Main Street and Fowler Avenue Durham, CT

Filled with rides and games, tractor pulls, three livestock barns, crafts, exhibits featuring baking, canning, photography and horticulture, and a wide selection of fair food, the Durham Fair is Connecticut’s largest agricultural fair. This year there will also be a Demolition Derby, tractor pull, live music/shows, and fireworks and laser lights shows.

Harwinton Fair

October 1-3, 2021 Harwinton Fairgrounds 150 Locust Rd. Harwinton, CT


Harwinton Fair, originally known as Harwinton Cattle Show and Fair, is the yearly event of the Harwinton Agricultural Society. There will be Pig Races, Antique Tractor Show, Rabbit Costume Contest, Oxen Draw and Civil War Displays. Enjoy a magic show and bluegrass music after visiting the barnyard animals. Don’t forget to stop by the Country Store.

Portland Fair

October 1-3, 2021 Exchange Club Fairgrounds Rte. 17A Portland, CT

Livestock Shows, Bands, Truck & Tractor Pulls, Mug Bog, Live Music, Fair Food, Midway Rides, Ground Entertainment, Vendors, heated entertainment, beer & wine Tent, and much more!


Valid: 01/01/1970 - 01/01/1970

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