FridayDoors 5:30 p.m.; dinner about 6:00 p.m.Brooklyn
Harvest & Harmony Farm Dinner
Little Dipper Farm, 499 Wolf Den Road
Multi-course dinner with the Evan Gianfreddo Jazz group.
$125; ticket purchase required; age guidance not stated.
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September 25, 2026
September 26, 2026
SaturdayDoors 12:00 p.m.Putnam
Bravofest
Charlee Bravo's, 9 Grove Street
Multi-genre music benefit for Homes For Our Troops; food included. The beneficiary's registration page says noon, which controls over a 1:00 p.m. publicity release.
$15 advance / $20 door; free for veterans, active military, and first responders; 21+ with ID.
Music & ArtsView source
Saturday7:00–9:00 p.m.Pomfret
Poets at Large
Vanilla Bean Café, 450 Deerfield Road
Poetry and poet-musician program with an open-mic opportunity.
Suggested $10 donation; ages 16+.
Music & ArtsView source
September 27, 2026
Sunday12:00 p.m.; end time not statedPutnam
Makers Market: Montana Nights — last call for vendors
Montana Nights, 50 Providence Pike
Makers market at Montana Nights. Last call for vendors: a 10x10 space is $45 for this event only, and vendors get a vendor spotlight in the paid event advertisement.
Vendor payment must be made by 5:00 p.m. Friday, September 18 to be added to the roster. Vendors can sign up on the vendor spotlight page at /vendors.
September 30, 2026
Wednesday5:30–6:30 p.m.Danielson
The Beatles
Killingly Public Library, 25 Westcott Road
Multimedia talk using visuals and recordings.
All ages; cost and registration not stated.
October 2, 2026
Friday6:00–9:00 p.m.Pomfret
Redcoats, Rebels, and Rev'rie Tavern Night
Vanilla Bean Café, 450 Deerfield Road
Revolutionary Pomfret kickoff with a tavern menu and sea shanties and tavern songs by Rick Spencer and Dawn Indermuehle.
$10; age guidance not stated.
Friday7:30 p.m.; doors 6:30, seating 7:00Woodstock
Magic of Motown
Loos Center for the Arts, 150 Route 169
Two-set Motown revue with an intermission.
$49–$69; ages 4+.
Music & ArtsView source
Friday6–9 p.m.Woodstock
40 Years of Service Free Concert — The Great Garage Band
NEPS, 312 Route 169, South Woodstock
Free outdoor concert marking NEPS' 40th year, with The Great Garage Band.
Free. Bring chairs and a picnic dinner.
Music & ArtsWINY: Here's What's Happening
October 7, 2026
Wednesday1 p.m.Danielson
Afternoon Movie: 9 to 5
Killingly Community Center, 185 Broad Street
Afternoon movie screening at the community center. Running time 1 hour 50 minutes.
Cost and registration not stated.
Music & ArtsWINY: Here's What's Happening
October 10, 2026
Saturday9:00 a.m.–5:00 p.m.; ceremonies 10:00 a.m.Brooklyn
Scotland Highland Festival and Games
Brooklyn Fairgrounds, 15 Fairgrounds Road
Highland athletics, piping, dance, music, heritage activities, food, vendors, and storytelling.
$25; $20 veterans/students/seniors; $5 ages 5–12; under 5 free; organizer currently says bring $5 cash for parking.
Saturday1:30–4:30 p.m.; finale 7:30 p.m.Woodstock
Layālaya Global Arts Festival
Loos Center, 150 Route 169
Global arts program with artists from six countries and Woodstock Academy student ensembles; October 7–9 activities have not been announced and are omitted.
Afternoon $10; evening $30/$45; afternoon add-on $5; ticket required; general guidance 4+.
Music & ArtsView source
October 11, 2026
Sunday2:00 p.m.Brooklyn
Ghost Stories to Scare the Dickens Out of You
Putnam Elms, 191 Church Street
Charles Dickens ghost-story portrayal. A separate 1:00 p.m. Preservation Connecticut member tour requires registration.
Free public performance; no registration; children welcome.
October 14, 2026
Wednesday1 p.m.Danielson
Afternoon Movie: The Life List
Killingly Community Center, 185 Broad Street
Afternoon movie screening at the community center. Running time 2 hours 5 minutes.
Cost and registration not stated.
Music & ArtsWINY: Here's What's Happening
October 16, 2026
FridayTime as listed by the libraryPomfret
Autumn Poetry Workshop
Pomfret Public Library, 449 Pomfret Street
A guided poetry writing workshop for adults.
Cost not stated. Registration may be required — call the library.
October 17, 2026
Saturday10:00 a.m.–3:00 p.m.Brooklyn
Little Dipper Farm Harvest Festival
499 Wolf Den Road
Farm festival with the John Spignesi Band.
Cost, registration, and age guidance not published.
October 17–18, 2026
Saturday–Sunday10:00 a.m.–4:00 p.m. both daysWoodstock
Roseland Cottage Fine Arts & Crafts Festival
556 Route 169
Juried show with 180 artisans, live music, food vendors, and first-floor cottage tours; rain or shine.
Historic New England members free; nonmembers $5; children under 12 free; outdoor uneven terrain.
October 21, 2026
Wednesday1 p.m.Danielson
Afternoon Movie: Sarah's Oil
Killingly Community Center, 185 Broad Street
Afternoon movie screening at the community center. Running time 1 hour 44 minutes.
Cost and registration not stated.
Music & ArtsWINY: Here's What's Happening
October 24, 2026
Saturday7:30 p.m.Woodstock
Double Vision — The Foreigner Experience
Loos Center for the Arts
Foreigner tribute concert at the Loos Center.
Tickets on sale soon; prices not stated.
Music & ArtsWINY: Here's What's Happening
October 28, 2026
Wednesday1 p.m.Danielson
Afternoon Movie: The Curse of Bridge Hollow
Killingly Community Center, 185 Broad Street
Afternoon movie screening at the community center. Running time 1 hour 31 minutes.
Cost and registration not stated.
Music & ArtsWINY: Here's What's Happening
October 30 and 31 and November 1, 2026
FridayOctober 30 and 31 at 7 p.m.; November 1 at midnightPutnam
Richard O'Brien's The Rocky Horror Show
The Bradley Playhouse, 30 Front Street
The Rocky Horror Show at the Bradley Playhouse, including a midnight Halloween-night performance.
Ticket prices not stated in the listing.
Music & ArtsWINY: Here's What's Happening
November 7, 2026
Saturday7:30 p.m.Woodstock
A Tribute to Taylor, Simon and King: 3 American Troubadours
Hosted by the Loos Center for the Arts
Tribute concert starring James Gedeon, Lisa Sherman and Alice Leon.
Tickets on sale soon; prices not stated.
Music & ArtsWINY: Here's What's Happening
Saturday6 p.m.North Grosvenordale
Dueling Pianos featuring Savage Pianos
The Raceway Restaurant and Banquet Hall, Thompson
Dueling pianos night benefiting Day Kimball Health At Home.
Ticket prices not stated.
Music & ArtsWINY: Here's What's Happening
November 14, 2026
Saturday7:30 p.m.Woodstock
Bruce in the USA
Loos Center for the Arts
Bruce Springsteen tribute concert at the Loos Center.
Tickets on sale soon; prices not stated.
Music & ArtsWINY: Here's What's Happening
January 29 – February 7, 2027
FridayShow times not statedPutnam
Ken Ludwig's A Comedy of Tenors
The Bradley Playhouse, 30 Front Street
Bradley Playhouse 2027 season opener.
Tickets never cost more than $37.
Music & ArtsWINY: Here's What's Happening
April 23 – May 9, 2027
FridayShow times not statedPutnam
Anastasia the Musical
The Bradley Playhouse, 30 Front Street
Bradley Playhouse production of Anastasia the Musical.
Tickets never cost more than $37.
Music & ArtsWINY: Here's What's Happening
June 3–6, 2027
ThursdayShow times not statedPutnam
R&J: Romeo and Juliet
The Bradley Playhouse, 30 Front Street
Bradley Playhouse production of Romeo and Juliet.
Tickets never cost more than $37.
Music & ArtsWINY: Here's What's Happening
July 23 – August 7, 2027
FridayShow times not statedPutnam
Come From Away
The Bradley Playhouse, 30 Front Street
Bradley Playhouse audience-choice production of Come From Away.
Tickets never cost more than $37.
Music & ArtsWINY: Here's What's Happening
October 9–25, 2027
SaturdayShow times not statedPutnam
Arsenic and Old Lace
The Bradley Playhouse, 30 Front Street
Bradley Playhouse audience-choice production of Arsenic and Old Lace.
Tickets never cost more than $37.
Music & ArtsWINY: Here's What's Happening
December 3–19, 2027
FridayShow times not statedPutnam
Scrooge & Marley: A Christmas Carol
The Bradley Playhouse, 30 Front Street
Bradley Playhouse holiday production adapted from Dickens.
Tickets never cost more than $37.
Music & ArtsWINY: Here's What's Happening
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