Living Well in Litchfield County, Connecticut

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Litchfield County June Events Not to Miss – Editor’s Picks

ASAP Community Party – June 4

ASAP!’s annual fundraising gala celebrates community with a festive evening hosted by actor and producer Tim Daly. There will be live music, beautifully crafted local food and an open bar.

Great Country Mutt Show @ Lime Rock Park – June 5

Free and open to the public, the Great Country Mutt Show is a Westminster-style Dog Show that celebrates all breeds. Held rain or shine at Lime Rock Park.

Music Mountain Concert – June 5

Don’t miss Music Mountain’s 93rd Season Opening Benefit Concert featuring the Rolston String Quartet and Paul Neubauer on viola. There will also be German food trucks!

Kent Fireman’s Ball – June 11

Enjoy a night of dancing, dinner, food, and community at the Kent Volunteer Fire Department’s annual ball. There will be raffles with a variety of prizes and a live DJ. Tickets and further information are available at

Gunn Memorial Library Annual Fundraiser – June 11

Start your evening with cocktails at the Gunn Memorial Library then head to a private dinner with engaging conversation and the company of a 2022 Library Luminary.

Art Tripping – June 11

Art Tripping brings the Litchfield Maker’s Market to the Litchfield Green. The weekend-long event will feature artists, craftspeople, demonstrations, and family-friendly activities.

Kent Singers Messiah Concert – June 12
The Kent Singers will perform the complete Messiah by Georg Friedrich Handel in entirety with a Baroque orchestra and professional soloists at St. John’s Episcopal Church in New Milford, conducted by music director James Knox Sutterfield. Tickets and further information are available at 860-619-8110 or at

SHAG Festival – June 16-19

Celebrate with SHAG at Spring Hill Vineyards and immerse yourself in four days of nature, creativity, and collaboration. This year’s festival features a great lineup of performers, food, and drink vendors.

Books & Blooms – June 17

The Cornwall Library’s biggest fundraiser of the year is the annual garden tour known as Books & Blooms. This year, the renowned garden writer Page Dickey will kick off the festivities with a presentation entitled “Bringing Meadows into the Garden.” On Saturday, the fun continues with some truly magical gardens to inspire visitors. A special addition to the mix this year are the gardens of the legendary Cornwall Castle which has been featured on the cover of Litchfield Magazine. Following Page Dickey’s presentation, there will be a Cocktail Reception outside the library under a tent, for ticket holders of the talk and sponsors of Books & Blooms.

Ticket Information:
Tickets $30 for the talk, $30 for the garden tours or $50 for both.
Please register and purchase on the website or contact the library.

Ripley Waterfowl Annual Benefit – June 18

An evening filled with live music, cocktails & hors d’oeuvres, featuring a catered summer dinner, open bar, and auctions in support of the Conservancy’s mission.

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