Rick’s Picks: Things To Do In Fairfield in September


Half Step – Grateful Dead Tribute

September 6

Half Step is a group of dedicated fans & students of the Grateful Dead, capturing the spirit, improvisation, sound & complexity of Grateful Dead music. Established in 2004 Half Step has been mastering their craft while winning over crowds of veteran Deadheads, newcomers and non-Dead fans alike.

Norwalk Oyster Festival

September 6 – 8

Oyster Festival attendees will have plenty of entertainment and activities to choose from over the weekend including the Nerveless Nocks Thrill ShowPaul Bunyan Lumberjack Show, a Kids’ Cove with rides, games and other child-centered live entertainment, a Craft Beer tent with more than 40 beers and the expansive Arts & Crafts Pavilion with more than 100 artisans and crafters. Plus, an international food court, oyster slurping contest, and much more.

Fairfield Light Up The Night Festival

September 7

The short car ride to Lake Mohegan is worth it for this annual tradition. The Fairfield Light Up the Night Festival brings everyone together for a beautiful and memorable night. A ticket includes entry and a water lantern kit.

Apple Festival

September 7-8

St. Peter’s Annual Apple Festival is the perfect way to kick-off New England’s fabulous fall season, with more than 100 craft vendors, food tent, Apple Central with apples, apple pies, and apple-themed items for purchase, Country Kitchen offering homemade baked goods, children’s games, prizes, face painting, moon bounce, raffles, mum sale, and live music.

6th Annual Sanctuary Food Truck and Music Festival

September 8

It’s time for our 6th Annual Food Truck and Music Festival! Get ready for live music, your favorite local food trucks, yard games and more!


September 13 – 15

With fairs a summer must, this is your last chance to gaze at the carnival lights with a chicken leg in one hand and a deep-fried onion in the other.

Country Rocks the Park Music & BBQ Festival

September 14 – 15

Two days of country music featuring live performances by Earl Dibbles, Jr., Willie Jones, Seaforth and more. There will be more than 20 of the area’s best restaurants and food trucks serving up barbecue and more, plus a beer garden. 

2nd Annual Connecticut Ukulele Festival

September 21

The concert will be the culmination of a full day of ukulele and music, food trucks, workshops, strum-a-longs and our first “One Uke Minimum” cover song competition.

42nd Annual Harvest Festival of Arts & Crafts

September 22

Head on down to Stratford, CT for a wide variety of vendors, crafters, local artists, live music, great food, and homemade cheesecakes. Kids and family are welcomed with games and prizes in the kids area.

Local Happenings

Trivia at Mecha

September 2 & 9

Compete for prizes over 5 rounds of trivia questions at Mecha.

Bourbon Adventures

September 6

Celebrate National Bourbon Month with this kick-off party at Plan b!

Falling & Commitment at Rock Climb Fairfield

September 19

Take part in this mental training day for climbers by Dustin Portzline of Warrior’s Way. Learn to fall, trust your body, and climb through doubt!

Bark In The Park

September 22

Appreciate all furry friends at this event. Families and their pets can check out the agility course, adoption area, K9 demonstrations, vendor booths, and much more. Good thing The Circle is dog-friendly! 


Stand Up Paddleboard Yoga

September 8

Experience the beauty and the calming serenity of floating on the water as you mindfully flow through a yoga and meditation practice on board. Brand new to yoga or paddleboarding – or both? No problem! No experience necessary.

Corn Maze

September 20 – October 31

Find your way out of 4.5 acres of corn with 1.5 miles of trail, featuring a wild labyrinth of bewildering twists and turns through ten-foot corn stalks. Fun for all ages!

Bike / Hike The Beach

September 22

Enjoy a challenging tour or a more leisurely family ride/hike. Scenic routes pass through as many as five historic New England towns on the CT coast. Choose from well-marked rides of 10, 20, 45, or 62 miles or a 5K fitness walk.

Historical Bike Tour

September 22

Hosted by the Fairfield Museum & History Center and the Fairfield Bicycle and Pedestrian Committee, the tour will visit various points of interest and recount the stories of important families from Fairfield’s long history, many of whose names are still well documented on the streets and buildings of the town.

Ambler Farm Day

September 22

You won’t want to miss the chance to attend Ambler Farm’s annual fall festival in Wilton, CT. For $20 a family (cash only) attendees get to enjoy the Apple Slingshot, hayrides, Make-Your-Own-Scarecrow, crafts, the pumpkin patch, and much more!



Two Roads Comedy Night

September 6

A ticket to the Two Roads Comedy Night at the Two Roads Brewing Company in Stratford, CT will get you a 2 hour comedy experience and your first pint of beer. Don’t miss out on the chance for good laughs!

Fairfield Comedy Club

Every Friday & Saturday

The Fairfield Comedy Club delivers top comedy content to The Circle every Friday and Saturday. Checkout a few of our future guests:

September 20: Dave Hill–comedian, actor, writer and will take the stage in late September to deliver top comedy content. He has appeared on Netflix’s The Unbreakable Kimmy Schmidt, TruTV’s Comedy Knockout, Amazon’s The Tick, and so many more.

September 28: Mike Cannon’s recently released comedy album, I Think It Just Kicked In, reached Top 10 on The Billboard Charts. He was a finalist in the 2016 New York Comedy Festival’s “NY’s Funniest” contest, regularly appears on several Sirius/XM Radio shows, and hosts his own podcast called Irish Goodbye Podcast.