WEEK OF MAY 18 - MAY 24, 2026
From June 4 Information Session at Summer Programs in Massachusetts - TeenLife to Storytime with Stay & Play at Becket Athenaeum and Therapeutic Recreation - TR Walking Club Spring 2026 at Cheshire Community Events.
MONDAY - 5/18
Cheshire Community Events,
Cheshire
- 4:30pm - 6:00pm — Art Explorers - Art Explorers ♡ art explorers
- 4:30pm - 6:00pm — Drawing (Kids) - Drawing Fun & Games: Junior Games ♡ drawing fun games
- 6:15pm - 7:30pm — LEAD Youth Advisory Board 2025-2026 - LEAD Y.A.B. 2025-26 Member (Gr. 7-12) ♡ lead youth advisory
Family Attractions in Monterey County,
Monterey
- - name: Memorial Day Open House — TBA ♡ visit history
- - name: Monterey County Pops! Free Memorial Day Concert — TBA ♡ enjoy music
Lee Youth Association,
Lee
- 8:30am — LYA Hoop Camp 2026 - Boys and Girls entering grades 3 - 8 - WEEK #1 ♡ register now
- 8:30am — LYA Hoop Camp 2026 - Boys and Girls entering grades 3 - 8 - WEEK #2 ♡ register now
- 9:00am — LYA Hoop Camp 2026 - Boys & Girls entering grades K - 2 ♡ register now
Programs & Events - Clarksburg-Harrison Public Library,
Clarksburg
- 11:00am — Sensory Time ♡ sensory time
- 11:30am — Playtime ♡ playtime
- 3:30pm — STEAM ♡ steam
- 4:00pm — Monday Night Magic ♡ magic night
Williamstown Rural Lands Foundation,
Williamstown
- 9:00am - 3:00pm — Earth Explorers (1st-4th grade) ♡ explore nature
- 9:00am - 3:00pm — Wild Water (1st-4th grade) ♡ explore water
TUESDAY - 5/19
Alford Lake Camp - North Shore Kid,
Alford
—
Barnyard Story Hour at Appleton Farms at 10:30am
♡
story hour
Cheshire Community Events,
Cheshire
- 2:00pm - 4:00pm — Therapeutic Recreation - TR Afternoon Club Spring 2026 ♡ tr afternoon club
- 3:30pm - 4:15pm — Speed, Agility & Strength for Youth at Bergamo's Martial Arts - Speed, Agility & Strength Spring II 2026 ♡ speed agility strength
- 4:30pm - 5:00pm — Bergamo's Ninja-Fit - Bergamo's Ninja-Fit 3-5 yr (Tuesdays - Spring II 2026) ♡ ninja fit
- 4:30pm - 5:30pm — Golf Lessons - Golf Lesson - Juniors May 2026 ♡ golf lesson juniors
- 4:30pm - 6:00pm — Cartooning (Kids) - Cartoon Your Favorite Character! ♡ cartooning kids
- 4:30pm - 6:00pm — Painting (Kids) - Painting Techniques ♡ painting kids
- 5:00pm - 5:45pm — Bergamo's Ninja-Fit - Bergamo's Ninja-Fit 6-12 yr (Tuesdays - Spring II 2026) ♡ ninja fit
Family Nights - Otis Ridge,
Otis
- 5:30pm — Internet Safety Workshop ♡ internet safety
- 6:30pm — On Demand Girl Scouts Fired Up! ♡ girl scouts fired up
Jurassic Quest® - The #1 Dinosaur Experience in North Americ,
Richmond
—
Process Art Adventures – Chesterfield at 3:15pm, 4:15pm
♡
process art
March 26 › Family Services Playgroups ›,
Great Barrington
—
Brain Builders at 10:30am - 11:30am
♡
brain builders
Mason Library (Great Barrington),
Great Barrington
—
Brain Builders: Weekly Drop-In Fun at 10:30am - 11:30am
♡
brain builders
Monterey Family Fun,
Monterey
- 12:00pm — Storytime in Gonzales ♡ storytime
- 6:00pm — Pajama Storytime at Seaside Branch Library ♡ pajama storytime
North Adams Community Events,
North Adams
—
North Adams SteepleCats vs Mystic Schooners at 6:30pm, 7:30pm
♡
baseball game
Our Innovative Curriculum - Whole Child Education - MWJDS,
Sandisfield
—
Playgroup at 10:00am
♡
join in
Programs & Events - Clarksburg-Harrison Public Library,
Clarksburg
- 5:00pm — Art With Emily - Liquid Pouring Art ♡ art with emily
- 5:00pm — PAWS- Mountaineer Therapy Dogs ♡ paws therapy dogs
Summer Programs in Massachusetts - TeenLife,
Florida
- 05:00pm to 06:00pm — Virtual Career Changers Information Session ♡ register now
- 06:00pm — Stand Out to Admissions: How Volunteering Abroad Can Define Your College Application ♡ register now
- 08:00pm to 09:00pm — Laurel Springs Virtual Open House 6/2 ♡ register now
- 09:00am to 10:00am — 2026 Pre-College Summer Program Virtual Info Session ♡ register now
- 6:00 pm — Is Your Student Outgrowing Traditional School? It Might Be Time for a Change ♡ register now
WEDNESDAY - 5/20
Calendar - Peppermint Park Camping Resort,
Pittsfield
—
Fun on the Farm at 10:00am
♡
explore the farm
Cheshire Community Events,
Cheshire
- 10:00am - 11:30am — Homeschool Classes - Homeschool Artist Study (Ages 10-14) ♡ homeschool artist
- 10:00am - 11:30am — Homeschool Classes - Homeschool Artist Study (Ages 5-9) ♡ homeschool artist
- 3:45pm - 4:45pm — STEM Programs with CT STEM Academy - Highland: Robotics (Grades 4-6) - Spring 2026 ♡ stem robotics
- 4:30pm - 5:15pm — Therapeutic Recreation - TR Walking Club Spring 2026 ♡ tr walking club
- 4:30pm - 6:00pm — Board Games Afterschool Club (Gr. 3-6) - Board Game Afterschool Club - Spring 2026 ♡ board games club
- 4:30pm - 6:00pm — Clay - Clay Play ♡ clay play
- 9:00am - 10:00am — Trail Trekkers - Trail Trekkers: Wednesday 5/20/2026 ♡ trail trekkers
Home - Central Massachusetts - Challenge Island,
Clarksburg
—
Cherry Festival's Kids Cherry Town Fun Night - FREE EVENT! at 4:00pm, 7:00pm
♡
select
Jurassic Quest® - The #1 Dinosaur Experience in North Americ,
Richmond
—
Wonder-FULL Wednesdays – Toddler Program – Downtown at 10:15am, 10:45am
♡
wonder full wednesdays
Lenox Library,
Lenox
- - name: Layered Wooden Ocean Scene Workshop — TBA ♡ learn more
- - name: Macrame Wall Hanging Workshop — TBA ♡ learn more
- 10:00am — Maritime Museum Monthly Activities: Sea Creatures ♡ learn more
March 26 › Family Services Playgroups ›,
Great Barrington
—
CHP Play at 10:00am - 11:00am
♡
stockbridge play
Monterey Family Fun,
Monterey
- 10:15am — STEAM Thursday ♡ steam thursday
- 4:00pm — Storytime Jamboree ♡ storytime jamboree
Museum & Park Passes,
Adams
- 4:00pm — ART CLUB ♡ art club
- 4:00pm — Lego Club ♡ lego club
- 5:30pm — 6-Week Virtual Family Cooking Class ♡ cooking class
Programs & Events - Clarksburg-Harrison Public Library,
Clarksburg
- 11:00am — Ready for Kindergarten ♡ ready kindergarten
- 3:00pm — Let's Unwind ♡ let's unwind
- 4:00pm — Anime Club ♡ anime club
Stoneham Community Events,
Stockbridge
—
American Stories: Rebels and Revolutionaries of the Berkshires History Course at 11:00am
♡
history course
Summer Programs in Massachusetts - TeenLife,
Florida
—
Ask NYSID Students Anything! at 05:00pm to 06:00pm
♡
register now
THURSDAY - 5/21
Adult and Family Community Enrichment Programs - Berkshire S,
Alford
- 5:30pm — Cole Porter ♡ register here
- 5:30pm — Rodgers and Hart ♡ register here
David and Joyce Milne Public Library,
Williamstown
—
Birds of Summer with Naturalist, David Brown at 6:00pm
♡
free talk
Jurassic Quest® - The #1 Dinosaur Experience in North Americ,
Richmond
- 10:00am, 4:00pm — CMoR Pilot Homeschool Day – Chesterfield ♡ homeschool day
- 3:15pm, 4:15pm — Process Art Adventures – Downtown ♡ process art
- 3:30pm, 4:00pm — Bella Ballerina Pop-Up Dance Class – Chesterfield ♡ bella ballerina
March 26 › Family Services Playgroups ›,
Great Barrington
- 10:00am — Toddler Play ♡ toddler play
- 3:00pm - 4:00pm — Playroom Drop-In Hour ♡ playroom drop in
Stoneham Community Events,
Stockbridge
—
Ron Ramsay’s Berkshire Music Salon Series at 5:30pm
♡
music salon
Summer Programs in Massachusetts - TeenLife,
Florida
- 01:00pm — Laurel Springs Virtual Open House 5/21 ♡ register now
- 05:00pm to 06:00pm — Interior Design vs. Interior Decorating and Architecture Webinar ♡ register now
- 06:00pm to 07:00pm — June 4 Information Session ♡ register now
FRIDAY - 5/22
Adult and Family Community Enrichment Programs - Berkshire S,
Alford
—
TBA at - name: Family Game Night
♡
join us
Family Nights - Otis Ridge,
Otis
- 5:00pm — Bronze Patrol ♡ bronze patrol
- 5:30pm — Silver Patrol ♡ silver patrol
- 6:00pm — Gold Patrol ♡ gold patrol
Hancock Shaker Village,
Pittsfield
- 11:00am — Thanksgiving on the Farm ♡ thanksgiving
- 11:00am — Green Friday Hike ♡ go hiking
Jurassic Quest® - The #1 Dinosaur Experience in North Americ,
Richmond
- - name: Seymour Grooves with Books! – Downtown — TBA ♡ seymour grooves books
- 2:00pm, 4:00pm — Make and Paint Friday – Chesterfield ♡ make paint friday
- 3:30pm, 4:30pm — CultureFest with Cultural Encounters – Downtown ♡ culturefest downtown
March 26 › Family Services Playgroups ›,
Great Barrington
—
Growing Together: Infant Feeding Essentials at 10:30am - 11:30am
♡
growing together
Mason Library (Great Barrington),
Great Barrington
—
Legos at the Library at 4:00pm - 5:30pm
♡
legos library
North Adams Community Events,
North Adams
- 10:00am, 12:00pm — Home Town Hero Banner Ceremony ♡ celebrate heroes
- 5:00pm, 8:00pm — First Friday ♡ downtown fun
- 6:30pm, 7:30pm — North Adams SteepleCats vs Upper Valley Nighthawks ♡ baseball game
SATURDAY - 5/23
Alford Lake Camp - North Shore Kid,
Alford
- 10:00am — Turtle Time at IRWS ♡ turtle time
- 10:00am — CraneOutdoors: The Castle Hill Hike ♡ castle hill hike
- 9:00am — Family Day at the Bird Banding Station ♡ family day
Berkshire Botanical Garden,
Stockbridge
—
Plant the Camp Garden for Families at 10:00am
♡
plant garden
Calendar - Peppermint Park Camping Resort,
Pittsfield
—
Literacy in the Park at 10:30am
♡
stories songs art
David and Joyce Milne Public Library,
Williamstown
- 10:30am — Wild Edible and Medicinals Herb Walk with Jade Alicandro ♡ pre-register
- 8:00am — Spring Bird Walk with Naturalist, David Brown ♡ join us
Family Attractions in Monterey County,
Monterey
—
TBA at - name: Sea Slug Scavenger Hunt
♡
explore nature
Family Nights - Otis Ridge,
Otis
- 10:00am — MakerZone: TinkerFest ♡ makerzone tinkerfest
- 1:30pm — MakerZone: Trashion Fashion ♡ makerzone trashion fashion
Hancock Shaker Village,
Pittsfield
- 10:00am — Goat Yoga ♡ join in
- 10:00am — Food Workshop: Making Fruit Curds ♡ create
- 10:00am — Market or Harvest Basket ♡ create
- 10:00am — 28th Annual Country Fair ♡ fair fun
- 11:00am — Pumpkin Extravaganza – Family Day at the Village ♡ family day
Home - Central Massachusetts - Challenge Island,
Clarksburg
—
Challenge Island at the Cedar Polka Fest KIDS DAY at 12:00pm, 4:00pm
♡
select
MASS MoCA,
North Adams
- 10:00am — Community Free Day June 2026 ♡ join in
- 10:30am — Family Storytime ♡ story time
- 3:00pm — Arielle Twist: CHOPPED ♡ join in
Mason Library (Great Barrington),
Great Barrington
- 11:30am - 12:30pm — Toddler Play Time ♡ toddler play
- 11:30am - 12:30pm — Ramsdell LEGO Challenge ♡ lego challenge
North Adams Community Events,
North Adams
- 1:00pm, 4:00pm — Wellness Day ♡ feel good
- 6:30pm, 7:30pm — North Adams SteepleCats vs North Shore Navigators ♡ baseball game
- 9:00am, 1:00pm — Farmers Market ♡ fresh food
Our Innovative Curriculum - Whole Child Education - MWJDS,
Sandisfield
- - name: Christmas in July — TBA ♡ christmas fun
- 6:30pm — Live Music in the Hills ♡ live music
- 9:00am — Fishing Derby ♡ go fishing
Stoneham Community Events,
Stockbridge
- - name: Norman Rockwell’s Stockbridge Walking Tour — TBA ♡ walking tour
- 11:00am - 3:00pm — Service Heroes: Exploring Art and Community ♡ service heroes
West Stockbridge Public Library,
West Stockbridge
—
TBA at - name: TurnPark Summer Festival 2026 - Myth
♡
subscribe
SUNDAY - 5/24
Adult and Family Community Enrichment Programs - Berkshire S,
Alford
—
Every Body Bounces at 1:00pm
♡
register here
Family Nights - Otis Ridge,
Otis
- 11:00am — Camp Lewis Perkins Open House ♡ camp open house
- 12:00pm — Daisies and Brownies Gardening for Good ♡ gardening for good
- 2:00pm — Juniors and Cadettes Gardening for Good ♡ gardening for good
Hancock Shaker Village,
Pittsfield
—
Celebrate the 200th Birthday of the Round Stone Barn at 11:00am
♡
celebrate
North Adams Community Events,
North Adams
- - name: ArtWeek Berkshires — TBA ♡ explore art
- 4:00pm, 6:00pm — North Adams SteepleCats vs Sanford Mainers ♡ baseball game
Our Innovative Curriculum - Whole Child Education - MWJDS,
Sandisfield
- 1:00pm — Live Music with the Meanies ♡ live music
- 2:00pm — International Art Show and Film Festival: Beyond Our Boundaries ♡ art fest
- 3:00pm — Ice Cream Social ♡ ice cream
Stoneham Community Events,
Stockbridge
—
TBA at - name: Kids Summer Sculpture Studio
♡
sculpture studio
Summer Programs in Massachusetts - TeenLife,
Florida
—
Summer Youth Leadership Academy at 9:30 am to 4:00 pm
♡
register now