October 2025 Concierge Calendar

Beyond Pumpkins

October is brimming with pumpkin spice and Halloween-themed activities, but Fairfield County offers much more this month! We've curated a list of events and ideas to enlighten, entertain, and inspire you, helping you and your loved ones to appreciate your home even more.

Click on any image below for more details — enjoy each

and every wonderful day!

10/1 Among the Vines

Sunset Zumba at Aquila's Nest Vineyards. Get ready to move, sweat, and have fun with easy-to-follow choreography that makes fitness feel like a dance party! Enjoy a glass of wine afterwards with your classmates.

10/2 Salsa, Anyone?

It's time to burn calories, not eat chips and salsa! This beginner-friendly dance class begins at 8pm, followed by two hours of dancing with fun DJs. Enjoy an Elicit beer or Mermaid Lemonade as a reward for all your effort.

10/3 Soaring!

Music on the Hill presents an uplifting and exhilarating concert celebrating the soaring human spirit. Experience this inspiring music from various eras at Norfield Congregational Church.

10/4 Book the Sitter!

Fall brings out the festivals, and it's hard to pick just one! Have a fun filled, adult Saturday:

Westoberfest in Westport

Woodside Bash at Earthplace

Oyster Festival - at Norm Blooms

10/5 Sunday Funday

Today's a perfect day to have a family fun day:

Ambler Farm Day, 25th Annual

St Francis Carnival in Weston

Earthplace Fall Festival

Southport Onion Festival

10/6 Fall Migration

Join expert conservationist, birder, master gardener and Wilton resident Joe Bear for this second in the free series of fall bird walks. 8-10am at Allen’s Meadow, registration required.

10/7 Perfect Pairings

Beer + Cheese? You bet! In this seasonal class at Fairfield Cheese Company you’ll dive into some captivating (old world and local) Oktoberfest brews, and enjoy expertly selected cheese pairings.

10/8 Viv's ~ Dairy Boy

If you know, you know. Viv's Veggies is a Weston institution. After partnering with Dairy Boy this season, the secret is out! Weekends are packed, Wednesday are better (12 - 5pm).

10/9 Chat & Create

Spend an evening with friends and neighbors, while working on your projects. Celebrate your progress on old projects and get inspiration for new ones.

10/10 Foodie Friday

Westport's restaurant week is almost over. What new or favorite eateries have you enjoyed during this fabulous two week run? Book a reservation for tonight.

10/11 Stomp for Lachat

It's HOEDOWN time down on the Farm! Come kick up your heels with the Flying Fingers Jug Band, enjoy some mouth-watering barbecue and so much more. It's Lachat's annual FUNdraiser.

10/12 Pumpkin Patch

Warrup’s Farm will be open for pick-your-own pumpkins during October weekends. Check out this quieter, less busy experience that includes hayrides, popcorn, maple candy treats and more.

10/13 Fest of Stories

Westport's acclaimed StoryFest kicks off a week of events with author and Oscar-nominated filmmaker Julian Brave NoiseCat. Get NoiseCat’s highly anticipated memoir, We Survived the Night, one day before its national launch tonight at the Westport Library.

10/14 Thrills & Chills

Join author and suspense superfan, Julie Sarkissian, at the Pequot Library as she moderates conversations and readings with authors Samantha Shea, Eric Eichhorn, Elise Hart Kipness, and Victoria Buitron. Prizes for the best dressed literary characters!

10/15 Weekday Walks

The 300-acre Trout Brook Valley State Park can be accessed from Bradley Road in Weston. Explore over rugged hills and valleys, watching for wildlife & wetlands.

10/16 Select the Man

Three male candidates are vying for the office of Westport's First Selectman. Hear them debate tonight at Green's Farm Academy; a Westport Journal Live event.

10/17 Friyay!

Time to pack Fairfield University's Quick Center for Stand Up for Homes with Hope. General admission or VIP — either way you'll do good while having fun with Tom Papa, one of the country's leading comics.

10/18 Music of the Sea

The Norwalk Symphony, in collaboration with the Maritime Aquarium, will perform an unforgettable night of music inspired by the power of water - from Bridge over Troubled Water to Under the Sea. Enjoy!

10/19 Making Strides

For over 30 years, the American Cancer Society's walks have been raising funds to make strides against breast cancer. Get your pink on and join a team, donate or volunteer for today's event.

10/20 Just Say Yes

The closing event of StoryFest, featuring Shonda Rhimes, is sold out...but you can borrow a copy of her best-selling memoir at the library. At the library, check out the display in the Sheffer Gallery — Every Picture Tells a Story.

10/21 Lost Lear

Lost Lear is a moving and darkly comic remix of Shakespeare’s play told from the point of view of Joy, an elderly person with dementia. A remarkable play, tonight at Fairfield University's Quick Center.

10/22 Perfect Views

An easy, three mile trek out and back will take you to the tower at Sleeping Giant State Park. You'll be rewarded at the top with spectacular 360 degree views of Long Island Sound and the greater New Haven fall foliage.

10/23 Calling Jazz Fans!

Enjoy a delightful evening with the Hewitt-Torff Trio as they whisk you back to the Golden Era of Jazz. Hosted by the Pequot Library, this event is free but please register in advance.

10/24 At the Lake...

The Fairfield Park District presents a free drive-in movie at Lake Mohegan! Watch Miguel bring music back to life for his family while visiting Land of the Dead in this Disney Pixar classic.

10/25 Do You Dare?

Take a special tour of Oak Lawn Cemetery & Arboretum. Visit the final resting place for many notable local residents, including Mabel Osgood Wright, Jason Robards, and Mary Tyler Moore.

10/26 Trick-or-Treat

It's Halloween on the Green, at the Fairfield Museum and History Center. Come dressed in your best costume ready to enjoy trick-or-treating and other fun, halloween themed activities.

10/27 Education

The quality of education provided by a town is important for many reasons. Become an educated voter by attending tonight's debate featuring Westport Board of Education candidates.

10/28 Oscar Wilde

Oscar Wilde’s most famous comedy comes to the Playhouse for the first time! Season ticket holders can also enjoy Taste of Tuesdays with wine and food from a local restaurant at 6pm.

10/29 Natural Art

Immerse yourself in the nature and explore your creativity in this hands-on art class for adults at Wakeman Town Farm. As you weave leaves, stones & twigs into an art form, you'll become more mindful of our environment.

10/30 Flashlight Maze

On Halloween eve, head to Castle Hill Farm in Newtown for a night of fall fun. Fuel up with mouth-watering bbq or wood-fired pizza and prepare to get lost in the maze after dark! Enjoy live music, a bonfire and beverages too. Costumes encouraged!

10/31 Halloween

For those with young children, today's agenda is set! For other adults looking for some Halloween-type thrills without the costumes...it is opening night at Wilton Playshop for it's production of Sweeney Todd. Click the image on the left for ticket information.

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

KMS Team at Compass

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.

September 2025 Concierge Calendar

Falling for Autumn

September acts as a charming transition from summer's warmth to autumn's refreshing chill— a perfect month to venture out and discover new things in Fairfield County, CT. Our curated selection of events and ideas is designed to enlighten, entertain, and inspire you and yours.

Click on any image below for details — enjoy each

and every wonderful day!

9/1 Fall Flavors Return

Summer & ice cream simply go together. On this last unofficial day of summer, treat yourself to fabulous fall flavors at Ferris Acres. From Caramel Apple Pie to Oh Snap, it'll be hard to choose!

9/2 Grow Native

Thinking of planting, or replanting, a garden this year? Aspectuck Land Trust is taking orders now for native plants. They also have great garden plans on their website for inspiration.

9/3 Dine Out

Why not on Wednesday? Now in its 14th year, Fairfield Restaurants are offering some great deals.

Special prix fixe menus and other discounted lunch/dinner options are available at 25+ restaurants.

9/4 Cultural Preview

Part of Westport's draw is its wide range of sublime cultural experiences. Westport Journal’s "Fall 2025 Culture Preview," a KMS-sponsored event, will give you a glimpse of what's ahead.

9/5 Funny Friday

"The night is cheap but the laughs are not." Laughing Gas and City Comedy proudly present a night of comedy at Westport's VFW. Tickets, $20, are going fast, and seating is first come, first seated.

9/6 Date Nights

Kicking off Westport Country Playhouse's 2025-6 season is the internationally beloved story, Tuesday's with Morrie. This poignant theatrical event will be performed on 4 nights only!

9/7 Oyster Fest

Three days of fun, food and entertainment ends today at veteran's Memorial Park. Be sure to catch our drumming partner, David Weber and the Logical Pretzel Band at 4pm!

9/8 Recycle Right

Learn about the current state of waste management in Connecticut. Jennifer Heaton-Jones talks about the importance of recycling correctly, tonight at Wakeman Town Farm.

9/9 Lowrie Courts

Enjoy a game of pickelball as the crisp fall air sets in. The courts at Compo were recently named in Tom Lowrie's honor. Other courts are at Westport's Doubleday and Town Farms complexes and in Weston, at Bisceglie Park.

9/10 Stolen Lives

Exonerated after spending years on death row, Sunny Jacobs and Peter Pringle found each and have dedicated their lives to helping others who have similarly suffered. Free film screening tonight at SHU Theater.

9/11 DNR for EMS

Commemorate this important date with Fairfield County's Almost All Physician Rock Band - DNR. Performing tonight at the Levitt Pavilion, DNR honors First Responders everywhere and offers this concert in support of Westport Volunteer EMS.

9/12 Family Carnival

The Wilton Rotary Club is thrilled to announce the return of its Family Carnival. This beloved community event will take place from Friday, September 12, through Sunday, September 14, at the intersection of School Road and Danbury Road/Rte.

9/13 Lachat Meadow

To close out this year's Music in the Meadow series, Lachat Town Farm is pleased to announce the return of Stella Blue's Band. For six straight years they have entertained the Lachat Friends with faithful renditions of classic Grateful Dead music.

9/14 Farmers Market

Sundays thru Oct 12, the market supports local farms and food producers by bringing fresh offerings to the community. Fun extras like Edgewise Kitchen who will sharpen your knives and Cycl Crft, who performs mobile bike repairs, are onsite too.

9/15 Life's Pressures

Balancing work, societal pressures, children's safety, social media, and elderly care can be challenging. Local mental health professionals will share strategies to help you stay present and prioritize self-care. Tonight at Westport Library.

9/16 Weir Preserve

Step into nature and explore 10 trails throughout the 110 acres of the Weir Preserve. Take in the fresh air and the beautiful flora and fauna. The red and striped maples may even be showcasing some fall color.

9/17 Wallstreet Bulls

Visit the Lockwood-Matthews Museum and discover "The birth of Wall Street." Learn how this economic engine propelled many to new heights of prosperity, including a woman named Hetty Green and Jeremiah Hamilton, the first black millionaire in America.

9/18 The Virtuosi

Support the Norwalk Symphony. Three world-class musicians will perform tonight at the HMTX headquarters in Norwalk. The building is an architectural marvel, with rooftop garden and stunning interior spaces, this is a gorgeous setting for glorious music and sumptuous food.

9/19 Fall Flavors

Kick-start the fall season with exciting new flavors and fun! TastebudsCT presents a happy hour cooking class where you’ll learn to craft both savory and sweet bites and curate drinks for your next autumn gathering. A 21+ event at the Westport Library.

9/20 Barre, no Barre

Focus on flexibility and total body strengthening during this 45-minute class at Grace Farms. Barre is a blend of ballet, yoga and pilates. This class is part of the monthly movement series, designed in collaboration with the local Lululemon Ambassador.

9/21 Soundscapes

Sunday Soundscapes kicks off its third season at the Weston Library. Canta Libre, will perform live music specifically written for flute, harp and strings. Critically acclaimed throughout the Northeast, this ensemble has also performed at Lincoln Center.

9/22 Keep Calm

And color on! Reduce your heart rate, increase your respiratory sinus arrhythmia and feel less anxious. Give this fun activity a try, Mondays from 1 - 2pm at Fairfield Woods Library. Materials and calming music are provided. For adults 18+.

9/23 Dress to Impress

Fairfield Museum and History Center explores nearly 100 years of captivating fashion. Icons such as Coco Chanel and Jacqueline Onassis Kennedy set the bar high! Kids (4+) are invited to take a hands-on approach and make their own accessories.

9/24 Part of the Show

Asi Wind's "More Than Magic" is a captivating performance that highlights his artistic talents while exploring the human spirit. Hailed by the New York Times as “one of the great magicians of our time,” Wind expertly engages the audience.

9/25 Closer to Freedom

Enjoy a short play and readings from an anthology of poetry and prose by members of a writing workshop led by Chris Belden for ten years at Garner Correctional Institution, a maximum security prison in Newtown. Q & A will follow if time permits.

9/26 Evening Market

The last of 2025's Friday markets! These popular nights at Lachat Town Farm offer music, food trucks and a fabulous variety of local vendors. Come out from 4 to 8pm and enjoy — you may even find some KMS team members serving the signature drinks!

9/27 Book Sale

The Easton Library book sale will be in the community room during this weekend. Hours are: 9am - 4pm on Saturday; 11am - 4pm Sunday. Books, puzzles, CDs, DVDs and games too.

9/28 Foraging in Fall

Join Earthplace naturalist Siobhan Prout on a short walk outside and learn how to gather and prepare the edible foods growing in the Earthplace woods and gardens.

9/29 Apple Season

With the leaves beginning to fall, what better way to celebrate autumn then by picking your own apples with the family at Silverman's Farm!

9/30 Tequila Dinner

Join Greens Farms Spirits for a special tequila pairing and dinner to celebrate the release of their private La Pulga Reposado barrel. Tonight, 7pm, at The Clubhouse.

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

Reach out to chat!