165th Woodstock Fair Guide

165th Woodstock Fair returns to South Woodstock for five days over Labor Day weekend, September 3–7, bringing one of Connecticut’s oldest agricultural traditions together with major concerts, livestock shows, carnival rides, fair food and several new attractions.

The 2026 Main Stage lineup is unusually strong. Tonic headlines Friday night, Kool & the Gang takes over Saturday, Trace Adkins performs Sunday, and Beach Boys co-founder Al Jardine and the Pet Sounds Band close the Fair on Labor Day Monday. The Flying Wallendas and magician Leon Etienne also perform throughout the weekend.

All Main Stage entertainment is included with Fair admission.

But the Woodstock Fair is still, fundamentally, an agricultural fair. Livestock barns, dairy cattle, sheep, goats, rabbits, agricultural competitions and the historic Brunn Barn sit alongside the flashing lights of the Fiesta Shows midway.

For its 165th edition, the Fair is adding something new to that mix: Rustic Tap & Vine, a dedicated beer and wine area featuring Connecticut producers.

Here’s what to know before heading to South Woodstock.

When Is the 2026 Woodstock Fair?

The Woodstock Fair runs Thursday, September 3 through Monday, September 7, 2026 at the Woodstock Fairgrounds, 281 Route 169 in South Woodstock.

Opening times vary by day.

Thursday: 4 p.m.
Friday: Noon
Saturday: 9 a.m.
Sunday: 9 a.m.
Labor Day Monday: 9 a.m.

Thursday through Sunday, the Main Gate remains open until 9:30 p.m., with other gates closing at 9 p.m. Carnival rides and games continue until 11 p.m.

Monday operates on an earlier schedule. All gates close at 7 p.m., with carnival rides and games continuing until 8 p.m.

The barns and exhibition halls also have their own closing times, so visitors primarily interested in the agricultural side shouldn’t wait until late evening to explore them.

How Much Are Woodstock Fair Tickets?

Online general admission for 2026 is $16.95 for adults, including the processing fee.

Admission for active-duty military members with identification is $11.80, while seniors 65 and older with identification also pay $11.80 online.

Children 10 and younger are admitted free.

One of the biggest values in the ticket is the entertainment.

The major concerts, Flying Wallendas performances, Leon Etienne’s magic shows and other stage entertainment are included with paid Fair admission. There is no separate concert ticket required for Kool & the Gang, Trace Adkins, Tonic or Al Jardine.

Main Stage performances are general admission with no reserved seating.

Guests may bring folding chairs for the grass-covered area in front of the stage.

Friday Night: Tonic Headlines the Main Stage

Friday, September 4, starts the first full day of the Fair at noon.

The Flying Wallendas perform at 1 and 3 p.m., followed by Soul Afire at 5 p.m. and Leon Etienne’s Magic Rocks at 6:30.

Then the Main Stage shifts into ’90s alternative rock.

Tonic performs at 8 p.m.

Formed in Los Angeles in the 1990s, Tonic broke nationally with its 1996 debut album Lemon Parade. The record produced the band’s signature hit, “If You Could Only See,” along with “Open Up Your Eyes.”

The band’s success carried into subsequent albums, and Tonic earned two Grammy nominations for its 2002 album Head on Straight.

Friday also brings the Old Fiddlers Club of Rhode Island to Center Stage at noon, Soul Afire at 2:30 p.m., Leon Etienne at 3:45 and the Fair’s Country Karaoke Contest at 6.

Saturday Night: Kool & the Gang

Saturday brings the biggest dance party of the weekend.

Kool & the Gang headlines the Main Stage at 8 p.m. September 5.

Few bands arrive with a catalog more immediately recognizable at a fairground.

The group’s decades of funk, soul, R&B and pop produced “Celebration,” “Jungle Boogie,” “Ladies’ Night,” “Get Down on It,” “Too Hot,” “Cherish” and a long list of other hits.

The band’s history reaches back to Jersey City in 1964, making Kool & the Gang’s longevity particularly appropriate for the 165th edition of a fair that has built its own identity around tradition.

Saturday’s Main Stage begins much earlier.

The Flying Wallendas perform at 1 and 3 p.m. The Stevie Nicks Experience performs at 5, followed by Leon Etienne’s Magic Rocks at 6:30 and Kool & the Gang at 8.

Center Stage has its own schedule beginning with Quest Martial Arts at 10:30 a.m., followed by the East Woodstock Cornet Band at 11:30. Quest returns at 2 p.m., the Stevie Nicks Experience performs at 2:30, Leon Etienne appears at 3:45, and the Pop Karaoke Contest begins at 5.

Sunday Night Belongs to Trace Adkins

Sunday, September 6, turns the Main Stage toward country music.

Trace Adkins performs at 8 p.m.

The Louisiana-born singer has spent three decades in country music, with a catalog that includes “You’re Gonna Miss This,” “Every Light in the House,” “Ladies Love Country Boys,” “Songs About Me” and “Honky Tonk Badonkadonk.”

Adkins has also been a member of the Grand Ole Opry since 2003.

Before the headliner, the Flying Wallendas perform at 1 and 3 p.m. Nick Bosse and the Northern Roots take the stage at 5, followed by Leon Etienne’s Magic Rocks at 6:30.

Center Stage begins Sunday at 10 a.m. with Whitney Doucet, followed by Danielson Martial Arts at 11:15, another Whitney Doucet performance at noon, Danielson Martial Arts at 1:30, Nick Bosse at 2:30 and Leon Etienne at 4.

Al Jardine Closes the Fair on Labor Day

The final day gets an appropriate end-of-summer soundtrack.

Al Jardine of the Beach Boys and the Pet Sounds Band perform at 5:30 p.m. Monday, September 7.

Jardine was a founding member of the Beach Boys, singing and playing guitar as the group created one of the defining catalogs in American popular music.

His lead vocals include “Help Me, Rhonda,” while his decades with the Beach Boys connected him to records ranging from the early surf hits through Pet Sounds and beyond.

Monday’s Main Stage begins with the Flying Wallendas at 11:30 a.m. Leon Etienne performs at 12:30, the Wallendas return at 2, Red Light Band performs at 2:30, and Etienne returns at 4 before Jardine closes the 165th Fair.

The Flying Wallendas Perform Throughout the Weekend

The Flying Wallendas are more than another stage act on the schedule.

The Wallenda name has been synonymous with high-wire performance for generations, dating back to the European circus tradition that eventually brought the family to the United States.

Their appearances are spread throughout the Fair, making them one of the easiest major attractions to catch even if you’re attending primarily for something else.

They perform Thursday at 6 p.m.; Friday, Saturday and Sunday at 1 and 3 p.m.; and Monday at 11:30 a.m. and 2 p.m.

That gives visitors nine opportunities over the five-day Fair.

Leon Etienne Brings Magic to Multiple Stages

Another performer will be difficult to miss.

Leon Etienne’s Magic Rocks appears repeatedly on both the Main and Center stages.

Etienne has built his act around large-scale illusions, sleight of hand, comedy and rock-show energy rather than the quieter presentation of a traditional stage magician.

His national television appearances have included America’s Got Talent, where he became one of the show’s recognizable magic acts.

At Woodstock, he’s performing multiple times throughout Labor Day weekend, making his show one of the easier entertainment options to work into a full day.

Don’t Skip the Agriculture

It would be easy to look at a lineup containing Kool & the Gang and Trace Adkins and think of Woodstock primarily as a music festival with carnival rides.

That misses the heart of the Fair.

The Woodstock Fair describes itself as Connecticut’s largest agricultural fair, and its agricultural competitions remain a major part of the five-day event.

Friday begins with the Rabbit Exhibition and Sheep Show at noon, followed by the Goat Show at 1 p.m. and Youth Dairy Cattle Show at 3.

Saturday starts early with the Dairy Cattle Show and Rabbit Exhibition at 9 a.m., Youth Sheep Show at 9:30 and Sheep Lead Line at 6 p.m.

Sunday includes rabbits, sheep and goats in the morning and Beef Showmanship at 3 p.m.

Monday begins with the Beef Show and Rabbit Exhibition at 9 a.m., followed by the Sheep Show at 9:30.

The Youth Dairy Cattle Show on Friday is followed by showmanship and a costume class, while Sunday’s Beef Showmanship is followed by steer and costume classes.

Visit the Brunn Barn Museum

One of the best places to understand why the agricultural part of Woodstock matters is the Brunn Barn Museum.

The barn itself dates to 1822.

It was dismantled in 2004 and reconstructed at the Woodstock Fairgrounds in time for the 2005 Fair.

Inside, the focus is on New England’s agricultural past.

Antique farm equipment and tools help show how work was accomplished before tractors, combines and other modern machinery transformed farming.

The barn also hosts demonstrations and educational displays.

In a Fair increasingly filled with modern entertainment, the Brunn Barn provides a direct connection to the agricultural history that created events like Woodstock in the first place.

New for 2026: Rustic Tap & Vine

One of the biggest additions to the 165th Fair is decidedly more modern.

Rustic Tap & Vine debuts in 2026 as a new beer and wine destination inside the Fair.

The project was created in partnership with bankHometown, a division of TruNorth Bank, along with Taylor Brooke Brewery and Winery, Bear Hands Brewing Company and Black Pond Brewery.

The new attraction opens with the Fair at 4 p.m. Thursday.

Rustic Tap & Vine operates Thursday from 4–7 p.m.; Friday, Saturday and Sunday from noon–7 p.m.; and Labor Day Monday from noon–6 p.m.

For adults who remember when a fair beer meant little more than grabbing whatever was being poured at a concession stand, the dedicated space gives the 2026 Fair another distinct destination.

The Midway Is Back With Fiesta Shows

Fiesta Shows operates the Woodstock Fair midway, with rides ranging from family attractions to the sort of spinning machinery that looks much more entertaining from the ground depending on your tolerance for centrifugal force.

The expected 2026 lineup includes the Super Cyclone Coaster, Spider Wheel, Warrior, Top Gun, Thunder Bolt, Zero Gravity, Hyper Spin, Pharaoh’s Fury, Fire Ball, Spinning Coaster, Zipper, Starship Exodus and Hurricane.

There are also gentler options including the carousel, train, Crazy Bus, Rock’n Tug and slide.

Ride height requirements vary.

Individual ride credits will be available at the Fair, while advance unlimited-ride options are also available.

Ride Wristbands Can Save Money

If the midway is going to be a major part of your day, buying in advance can save a few dollars.

Thursday’s unlimited wristband is $30 online or $35 on site and is valid from 4–10 p.m.

Friday is split into two sessions, noon–5 p.m. or 5 p.m.–close, with wristbands costing $30 online or $35 on site.

Saturday, Sunday and Monday use all-day Megapass wristbands at $40 online or $45 on site.

These do not include Fair admission.

Wristbands and Megapasses also aren’t valid for the bumper cars, mechanical bull, rock wall or bungee jump.

Family Fun Goes Beyond the Midway

Families who don’t want to spend the entire day buying ride credits have another option.

The Fabulous Family Fun Area is open all five days with the Records and Burpee Petting Zoo, inflatable games and Sandtasia Sand Sculpture.

The Pork Chop Revue also performs throughout the weekend.

Despite the name, it’s not a barbecue demonstration.

The show features trained pigs performing tricks and comedic routines and has become the kind of oddball agricultural entertainment that fits naturally at a country fair.

Saturday also brings Vinny’s Pizza Eating Contest at 2:15 p.m.

On Sunday, the competitive eating turns to dessert with a Blueberry Pie Eating Contest at 2:15.

You Can Enter the Karaoke Contest

The audience can become the entertainment on Friday and Saturday.

Friday’s Country Karaoke Contest begins at 6 p.m. on Center Stage.

Saturday’s Pop Karaoke Contest starts at 5 p.m.

Each contest is limited to 10 contestants, and advance registration is available through the Fair.

Participants are asked to arrive at Center Stage 30 minutes before the contest, with registration beginning 15 minutes before showtime.

Someone can even enter both competitions, although a separate registration is required for each.

Labor Day Starts With a Cornhole Tournament

Monday morning brings a different kind of competition.

The Woodstock Fair Cornhole Tournament begins at 10 a.m. September 7 on Center Stage.

Two-person teams compete in either Social or Competitive divisions.

Registration is $50 per team, or $25 per player, and the entire registration pool goes into the prize purse.

The Woodstock Fair adds another $2,500.

Tournament registration does not include Fair admission or parking, and players need to bring their own regulation cornhole bags. The Fair supplies the boards.

Come Hungry

Woodstock’s food list is enormous.

This is still the place for fried dough, funnel cakes, sausage and peppers, giant eclairs, fried Oreos, caramel apples, ice cream, kettle corn and the sort of food decisions that seem completely reasonable inside a fairground.

But the selection goes considerably further.

There are lobster rolls and lobster quesadillas from Cousins Maine Lobster; clam cakes and chowder; jerk chicken and oxtails; Polish food including pierogi, kielbasa and stuffed cabbage; gyros; barbecue brisket; poutine; tacos; empanadas; Indian street food; Thai dishes; Colombian-American food; Mediterranean dishes; bubble tea and specialty coffee.

You can find bacon on a stick.

You can find chocolate-covered bacon.

You can find a deep-fried PB&J.

There is even a vendor dedicated entirely to gluten-free fair food, with gluten-free funnel cakes, fried Oreos, chicken tenders, corn dogs and donuts.

Local churches, Scouts, Lions, veterans groups and other nonprofits also operate food stands, continuing a piece of the Fair that feels considerably closer to its community roots.

Parking Is Not Included

This is important for first-time visitors.

The Woodstock Fair does not operate an on-site parking lot.

Instead, neighboring farms, businesses and organizations provide parking around the Fairgrounds and set their own prices.

For 2026, the Fair lists several nearby options at $10.

Fairvue Farm is on Route 171 near the South Gate.

Valleyside Farm is near Routes 171 and 169 and provides access convenient to the Main and Service gates.

South Woodstock Baptist Church offers parking near Roseland Park and North Gate roads.

Scranton’s Shops is across the street and diagonally north of the Service Gate.

Bring the extra $10 into your day’s budget rather than arriving expecting admission to include parking.

Plan on Walking

The Woodstock Fair is big.

Between the livestock areas, exhibition halls, stages, food stands, midway, agricultural attractions and parking outside the grounds, a visit can involve a considerable amount of walking.

Comfortable shoes aren’t a bad idea.

It’s also worth looking at the Fair map before arriving, particularly if you’re trying to catch a specific livestock show and a Main Stage performance on the same day.

The agricultural Fair and entertainment Fair coexist, but they’re not all concentrated into one compact midway.

Which Day Should You Go?

If music is the deciding factor, the choice is straightforward.

Go Friday for Tonic.

Go Saturday for Kool & the Gang.

Go Sunday for Trace Adkins.

Go Monday for Al Jardine and the Pet Sounds Band.

For the broadest all-day Fair experience, Saturday and Sunday provide early 9 a.m. openings and entertainment running into the evening.

Monday is a good choice for visitors who prefer an earlier day, with the Fair opening at 9 a.m. and winding down after Al Jardine’s 5:30 p.m. concert.

Thursday is the abbreviated opening night, beginning at 4 p.m.

And if the animals are your priority, check the livestock schedule before choosing a date. Different species and competitions take place on different days.

Event Details

Event: 165th Woodstock Fair
Dates: Thursday, September 3–Monday, September 7, 2026
Location: Woodstock Fairgrounds
Address: 281 Route 169, South Woodstock, CT 06267
Thursday Opening: 4 p.m.
Friday Opening: Noon
Saturday Opening: 9 a.m.
Sunday Opening: 9 a.m.
Monday Opening: 9 a.m.
Adult Online Admission: $16.95 including processing fee
Senior 65+ Online Admission: $11.80 with ID
Active-Duty Military Online Admission: $11.80 with ID
Children: Ages 10 and younger free
Main Stage Headliners: Tonic, Kool & the Gang, Trace Adkins, Al Jardine of the Beach Boys and the Pet Sounds Band
Other Major Entertainment: Flying Wallendas and Leon Etienne’s Magic Rocks
New for 2026: Rustic Tap & Vine
Midway: Fiesta Shows
Parking: Nearby independently operated lots; listed 2026 options are $10
Main Stage Shows: Included with paid Fair admission; general admission seating

More information is available at the Event Website link below.

To purchase tickets, click the Event Ticketing link below.

 

Featured image is an artistic representation inspired by the event and may not depict the actual people, location, or activities shown.