Concierge Calendar - May 2026

May Events Curated by the KMS Team at Compass

May is blossoming all around us! Enjoy our handpicked selection of events and activities crafted to inspire, entertain, and deepen your appreciation for the place you call home. Simply click any image below for more information. MAY 1 BACK TO 1776 We were fighting the British back then but Gruel Britannia is providing the fare for tonight's fireside dinner. Enjoy a special night at Lachat Town Farm, part of Weston's America 250 Celebration. MAY 2 TREASURE HUNT Our friends on The Nolan Team at Compass have organized a town-wide tag sale. With 40+ households on the list, you are certain to find something you need. Come shop Westport! Rain date 5/3. MAY 3 WALK 'N ROLL This STAR fundraising event supports early childhood therapies, transition for high school graduates, and life enrichment classes for adults with intellectual and developmental disabilities.

MAY 4 jedi training May the Fourth Be With You—funny, right? Bring your little Jedi-in-training, ages 5 to 10, to a special coaching session at the Bigelow Senior Center. Hosted by Fairfield Parks and Recreation. MAY 5 FARM TO TABLE Yep, it's Cinco de Mayo, and you can celebrate at Wakeman Town Farm with a special dinner. But if you live in Wilton, you should attend the Annual Town Meeting to vote on some important Ambler Farm Matters. MAY 6 Gun Violence Headlining this fundraiser for CAGV (CT Against Gun Violence) is Westport's own Josh Koskoff. Learn about his notable case victories while supporting this impactful state advocacy organization.

MAY 7 For The BOOKS This Westport Library event supports Read to Grow, an organization dedicated to fostering lifelong learning by promoting language skills, increasing book access, and supporting families as primary educators. MAY 8 Friday FUN Catch the antics of five crazy nuns from Hoboken as they try to raise money to save their convent and bury the last four sisters they have on ice. Guaranteed fun for the end of the work week! MAY 9 at the movies Lights. Camera. Action. delivers a thrilling tribute to iconic movie soundtracks and award-winning songs, featuring stunning harmonies, standout vocals, and unforgettable music. Tonight at SHU Theatre.

MAY 10 Treat Mom A scrumptious brunch is on order for all Moms today. We are partial to The Bridge at Saugatuck where the views are fine and the food is divine. Make your reservation! MAY 11 Summer in Pari? Make the most of summer's ingredients, French-style. Pan-roast chicken with a white wine sauce and steam artichokes. Create Lemon and Sugar Crêpes for a delightful finish. At Sur la Table, Darien. MAY 12 MAXIMUM Summer ”How to Enjoy Summer to the Max?” will be the focus of a Westport Journal roundtable discussion from 6:00 - 7:30 p.m. at the Cedar Point Yacht Club. Free event, sponsored by KMS, but please register. MAY 13 E-Bike Safety Wilton Library hosts a panel of experts to discuss strategies for keeping kids safer on the road, including visibility, movement indication, bike selection, and new Connecticut e-bike legislation. MAY 14 inDOOR Rain During The Big Bloom at Stepping Stones Museum in Norwalk, children can enjoy a sparkling bubble rain shower set to "Singin' in the Rain." Join the fun daily at 10:45 am and 1:45 pm. MAY 15 Bueller! The timeless favorite, Ferris Bueller's Day Off, is playing tonight on the Roger Ludlow Middle School Field! Grab your comfiest blanket, gather your friends, and get ready for an enjoyable, relaxing evening. MAY 16 CLick, CLack Moo After declaring the farm a tech-free zone, Farmer Brown encounters texting cows and striking chickens. Bring the kids to this musical comedy about negotiation and compromise at the Westport Playhouse. MAY 17 Spillway TOur Offered just a few times a month, this Sea Kayak Tour takes you along a serene stretch of the Saugatuck River. Paddle north past the Ruth Steinkraus Cohen Bridge, under the Kings Highway Bridge, and to the Wood Dam spillway. MAY 18 PAINT AND SIP Create this sunset scene with eye-catching poppies at Pinot's Palette in Stamford. Offering classes in their Harbor Point studio for more than a decade, this is a fun way to connect with friends, old and new! MAY 19 Storytelling Go behind the scenes with Roger Schulman, co-writer of Shrek, whose storytelling spans films like Balto, Mulan II, and The Jungle Book II, as well as series like Living Single. Schulman brings his decades of storytelling experience to the Trefz Forum stage. MAY 20 MOVIE MAGIC Musically rich and intellectually engaging, this program explores how classical music enhances film storytelling by adding emotional depth and drama. Presented by Joanna Chang, Assistant Professor at Fairfield University. MAY 21 EXPLORE NATURE A perfect way for kids (K-2) to unwind after school. Hike the Sanctuary trails to spot signs of wildlife, use nets to observe insects and pond creatures up-close, and enjoy hands-on science experiments. Registration required, at Fairfield Nature Center. MAY 22 Weston FAir Weston celebrates Memorial Day weekend (May 22-25) with a fair, 5K, and parade. This volunteer-run PTO fundraiser attracts thousands, with 100% of proceeds supporting local schools, benefiting Weston students. MAY 23 KICK OFF SUMMER Westport Parks and Rec kicks off summer at Compo Beach today with "Touch-a-Truck" featuring Police, Fire, EMS, and Public Works vehicles, along with face painting, obstacle courses, volleyball and more. Join the fun! MAY 24 Arts Festival Westport's 53rd Fine Arts Festival offers diverse artworks for all tastes and budgets, drawing artists and visitors from the Tri-State to New England. Food vendors, live music, and interactive art demonstrations too. MAY 25 Memorial Day 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 fire station. MAY 26 SAND CASTLES Get your little one ready for beach days with a story, gallery tour, and craft! Together, explore the Bruce Museum’s collections with some hands-on fun. Free with general admission, but space is limited. Sessions at 10 and 11am. MAY 27 Waterfalls Wander Indian Wells State Park. Nestled on the western bank of the Housatonic River in Shelton, the park features a stunning waterfall, a sandy beach, shaded picnic areas, and the only public boat launch on the river—ideal for a summery day. MAY 28 Taste of SoNo Experience a curated selection of Fairfield County's top restaurants and drink vendors while supporting CT Foodshare and your local community. The 2nd annual Taste of SoNo event will feature a silent auction, open bar, and live entertainment. MAY 29 Southing Sounds In honor of Mental Health Awareness Month, join this immersive sound meditation featuring crystal and Tibetan singing bowls, gongs, chimes, and more. A safe space to relieve stress, calm the mind, and reconnect with yourself. MAY 30 HISTORIC & RARE As part of America’s 250th anniversary, The Glass House will open the 1783 Grainger House and its renowned peony and iris garden for public tours. Originally known as the Finch House, it stands on one of New Canaan’s earliest registered land parcels. MAY 31 Prospect Garden Through the Garden Conservancy, this private Westport garden is open twice a year. Dating back to the 1812 original Victorian farmhouse and part of the Wakeman onion farm, this private property now includes almost 9 gorgeous acres.

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

KMS Team at Compass 203.295.4375 kmsteam@compass.com kmscompass.com

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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