Concierge Calendar - May 2025

May 2025 Concierge Calendar

May Flowers


May always seems to pass too quickly, with spring events filling every weekend. There's some weekday inspiration lined up for you here as well. We hope you grab a day here and there to savor life in Fairfield County, CT

Click on any image below for details — enjoy each

and every lengthening day!

5/1 Shop, Stroll, Sit?

Fairfield's Spring Shop & Stroll is today! You may find the perfect Mother's Day or graduation gift with in-store promotions. Enjoy the event happy hour at Ryebird (5-6pm) and shop 'til you drop (stores are open until 9pm).

5/2 And, Dance!

With their favorite adult, kids in grades k-8 are invited to dance the night away at Fairfield's Spring Fling. Dress up and head to Penfield Pavilion for a night of memory-making (7 - 9pm, registration required).

5/3 And They're Off...

It's Derby Day, even in CT! Put on your best attire and head to The Benjamin restaurant in Ridgefield for delicious food, music and a festive atmosphere. Or catch the "Run for the Roses" at the Pequot Library fundraiser in Southport.

5/4 EcoFest

An environmental education, service & celebration day. Bring your redeemables to contribute to Weston's 1 millionth bottle and can collection. Lachat Town Farm packs the day with music, food & activities for the whole family.

5/5 Calling All Dogs

Weston’s new dog park is set on 2.8 acres in the middle of 36 acres the town acquired decades ago. From its entrance on Lords Highway East dogs now have room to roam.

5/6 New Canaan Tea

All event proceeds (including shopping & flower bar) support Blossom Hill’s mission of childhood education for peace & fellowship in war-torn areas in the Middle East/North Africa.

5/7 Girl's Night Out

Learn the art of floral design from an award-winning designer, while enjoying light bites and beverages at the Fresh Flower Bar. Perfect preparation to help you make the most of the spring blooms popping up all around us.

5/8 Mocktails!

Join Leah Jones in crafting and sipping delicious mocktails! Making these seasonal beverages, inspired by Grace Farms Tea & Coffee, will broaden your understanding of the ways food intersects with our lives.

5/9 Do it Again

Logical Pretzel Steely Dan Tribute Band is opening its 2025 concert season at Sugar Hollow Taproom in Danbury. This ticketed event is a great way to see our partner, David Weber. Another is to catch him at an open house!

5/10 Dogwood Festival

Crafts fair and more including food trucks and baked goods, live music and live plants. So much happening in Fairfield's Greenfield Hill this weekend but the dogwood blossoms — pink and white, are the real stars.

5/11 Mother's Day

If you’re looking for a day of thrill-seeking fun rather than a tasty brunch, head to the trees where Moms climb free! Weave through the ropes courses and fly on the ziplines, challenge awaits at The Adventure Park.

5/12 Giving Back

This expo at Westport Library is a great place for teens to discover a cause or an organzation that speaks to them. Homelessness, hunger, equestrian therapy — there's a variety of agencies seeking volunteers.

5/13 Rules & Regs

A community conversation on the subject of Ebikes. Join the Westport Police at 6:30pm in Town Hall to hear the evolving rules & regulations surrounding these personal mobility devices. For the safety of riders and others, let's learn together.

5/14 Wine Down

Join Yard House, Pinstripes, Bazille, and Uncle Seven every Wednesday from 5 PM – 8 PM for Wine Down Wednesday at The SoNo Collection. Enjoy a relaxing evening with friends and family while sipping delicious wines, whiskeys, beer, or mocktails.

5/15 Wilton Farmers

It's baseball season! Did you know Wilton once had a semi-pro team? Wilton Historical Society's director Nick Foster will tell of their cinematic origin, local dominance and their unique home field. Tonight 6:30pm

5/16 Comedy Night

Rowayton's legendary comedy nights return to the Community Center (6:30PM). Partnering with New York Comedy Club, these events will be a blast. Grab a table for your besties & get ready to laugh.

5/17 Garden Envy

Sleepy Cat Farm has a multitude of garden rooms, full of unique elements, including a Japanese spirit bridge and 10,000 Japanese Iris. Tour today as part of the Garden Conservancy Open Days. The 13+ acres of this Greenwich estate will not disappoint!

5/18 Dog Festival

9th year! Over 1,000 dogs are expected at the best Dog Festival in the State. Come on out for a great day in Westport's Winslow park with competitions, obstacle courses, K9 presentations, demonstrations and more. Fun for all... including people.

5/19 Book Sale

It's bargain day! The Westport Library book sale started on Friday and winds up today. Pick up a logo sack and fill it with books for $10, or bring your own to fill for just $8.

5/20 Page Turners

Join the book group at Westport Library as they discuss The Only Woman in the Room by Marie Benedict. New members are welcome. Meetings are monthly, on the 3rd Tuesday at 11am.

5/21 Garden Adventure

The New York Botanical Garden welcomes children back to the Everett Adventure Garden with special activities daily. Roam the boardwalk, play instruments and make seed confetti. Everyday is a great day at NYBG!

5/22 Film Screening

Experience Penelope Spheeris’ 1983 Suburbia, as the film follows a young man who finds refuge among a group of social outcasts. After the screening at MOCA/CT, stay for a brief Q&A with film critic Susan Granger.

5/23 Memorial Fair

Annually, Weston celebrates Memorial Day weekend with a fair, 5K and a parade. Attracting thousands of Westonite families and those from surrounding communities, the fair is run by volunteers from the PTOs and it is their largest fundraiser of the year. May 23 - 26th.


5/24 Antique Cars

Come see the early brass cars (1900 - 1915) and watch a demonstration of how they climbed Sport Hill back in the day. Today's Sport Hill Races start at the Easton Library and head up Morehouse Road. Display cars (~40) will be on hand from 10am - 2:30pm.

5/25 Art of Westport

Westport Fine Arts Festival celebrates its 52nd Anniversary! This festival is a notable highlight for collectors and residents from the Tri-State region, New England, and beyond. All artwork is available in various price ranges, subject matter, and styles.

5/26 Honor, Celebrate

Westport's parade kicks off at 9am, with a service following on Veteran's Green. Fairfield and Norwalk parades start at 10am. Wilton's 10am parade is followed by a service at Hillside Cemetery. Weston's parade typically ends at the volunteer fire station.

5/27 Just like the Pros

Learn the art of the sushi roll tonight at Elicit Brewing as Chef Jay guides you through the process. Make a vegetarian and a California roll, while sipping a craft beer or glass of wine.

5/28 Local Artists

The Pequot Library proudly displays the artwork of Fairfield students from May 16-29th, during normal business hours. Tonight, from 5 - 9, is a reception honoring the K-12 aritsts.

5/29 Thursday are Fab

Westport Farmers' Market is back!

Thursday's 10am - 2pm in the Imperial lot. Also, returning in Fairfield is music at the Gazebo. Tonight Ace & Friends play Grateful Dead and other alternative rock classics.

5/30 Pollinator Party

Parents can enjoy a night out while their kids enjoy a night in (6-9pm) at Earthplace! The kids will explore Animal Hall and the meadows, learning about the various pollinators that are vital to our ecosystems and food supply for human and wildlife.

5/31 Cocktails & Clams

A truly unique event! Join Copps Island Oysters on Norwalk Harbor from 5-7pm, in a benefit for Harbor Watch. Enjoy an unlimited raw bar, hors d'oeuvres, open bar, live band and silent auction. Adults (21+) only, please.

Newcomer or long-timer, we hope you all find something new to enjoy near home this month.

Compass Connecticut, LLC is a licensed real estate broker. All material is intended for informational purposes only and is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. No statement is made as to the accuracy of any description or measurements (including square footage). This is not intended to solicit property already listed. No financial or legal advice provided. Equal Housing Opportunity. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.
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