Travel & outdoor events in Pittsfield, MA

Search for something you love or check out popular events in your area.

Just added!
CT Trails Day Hike
Sat, Jun 7, 9:00 AM
Herrick Trail Preserve
Just added!
CT Trails Day Hike
Sat, Jun 7, 9:00 AM
Herrick Trail Preserve
Trails Day Paddle - Wethersfield Cove
Sun, Jun 8, 10:00 AM
Wethersfield Cove
Trails Day Paddle - Wethersfield Cove
Sun, Jun 8, 10:00 AM
Wethersfield Cove
Keene Outdoor Craftfest & Classic Car Exhibition 2025
Sat, Jun 14, 9:00 AM
Keene Middle School
Keene Outdoor Craftfest & Classic Car Exhibition 2025
Sat, Jun 14, 9:00 AM
Keene Middle School
Selling quickly
2025 Kids Fishing Derby
Sat, May 3, 8:15 AM
Fitzwilliam Town Hall
Selling quickly
2025 Kids Fishing Derby
Sat, May 3, 8:15 AM
Fitzwilliam Town Hall
Monday Intermediate ride, Quillinan Reservoir
Mon, May 12, 5:30 PM
Rimmon Rd - Route 313 Ansonia
Monday Intermediate ride, Quillinan Reservoir
Mon, May 12, 5:30 PM
Rimmon Rd - Route 313 Ansonia
Sales end soon
Scavenger Hunt Worcester
Today at 2:00 PM + 61 more
Worcester
Sales end soon
Scavenger Hunt Worcester
Today at 2:00 PM + 61 more
Worcester
Sales end soon
You Sleuth Augmented Reality Detective Experience
Today at 2:00 PM + 162 more
Worcester
Sales end soon
You Sleuth Augmented Reality Detective Experience
Today at 2:00 PM + 162 more
Worcester
Moonlight Night Hike
Sat, May 10, 8:00 PM
Ansonia Nature & Recreation Center
Moonlight Night Hike
Sat, May 10, 8:00 PM
Ansonia Nature & Recreation Center
Guided Spring Bird Walk: Haddam Meadows State Park
Sat, May 17, 8:30 AM
Haddam Meadows State Park
Guided Spring Bird Walk: Haddam Meadows State Park
Sat, May 17, 8:30 AM
Haddam Meadows State Park
Sales end soon
Easter Morning Wildflower Walk at Distant Hill Nature Trail
Sunday at 9:00 AM
Distant Hill Nature Trail
Sales end soon
Easter Morning Wildflower Walk at Distant Hill Nature Trail
Sunday at 9:00 AM
Distant Hill Nature Trail
Sales end soon
Easter Afternoon Wildflower Walk at Distant Hill Nature Trail
Sunday at 1:00 PM
Distant Hill Nature Trail
Sales end soon
Easter Afternoon Wildflower Walk at Distant Hill Nature Trail
Sunday at 1:00 PM
Distant Hill Nature Trail
Distant Hill Pavilion Celebration with 'The Caterpillar Lab'
Sat, Jun 14, 12:00 PM
Distant Hill Nature Trail
Distant Hill Pavilion Celebration with 'The Caterpillar Lab'
Sat, Jun 14, 12:00 PM
Distant Hill Nature Trail
Insect Tracking Walk as part of our Pavilion Celebration at Distant Hill
Sat, Jun 14, 1:00 PM
Distant Hill Nature Trail
Insect Tracking Walk as part of our Pavilion Celebration at Distant Hill
Sat, Jun 14, 1:00 PM
Distant Hill Nature Trail
NEMBA Adventure Series - Pomfret Fun Ride
Sun, Sep 21, 9:00 AM
Pomfret Recreation Park
NEMBA Adventure Series - Pomfret Fun Ride
Sun, Sep 21, 9:00 AM
Pomfret Recreation Park
Selling quickly
Summer Nature Days: Week of July 14th to 18th
Mon, Jul 14, 9:00 AM
Ansonia Nature & Recreation Center
Selling quickly
Summer Nature Days: Week of July 14th to 18th
Mon, Jul 14, 9:00 AM
Ansonia Nature & Recreation Center
Just added!
Summer Nature Days: Week of July 21st to 25th
Mon, Jul 21, 9:00 AM
Ansonia Nature & Recreation Center
Just added!
Summer Nature Days: Week of July 21st to 25th
Mon, Jul 21, 9:00 AM
Ansonia Nature & Recreation Center
Just added!
Summer Nature Days: Week of Aug. 4th to 8th
Mon, Aug 4, 9:00 AM
Ansonia Nature & Recreation Center
Just added!
Summer Nature Days: Week of Aug. 4th to 8th
Mon, Aug 4, 9:00 AM
Ansonia Nature & Recreation Center
Just added!
Summer Nature Days: Week of Aug. 11th to 15th
Mon, Aug 11, 9:00 AM
Ansonia Nature & Recreation Center
Just added!
Summer Nature Days: Week of Aug. 11th to 15th
Mon, Aug 11, 9:00 AM
Ansonia Nature & Recreation Center
Foraging Walk
Sat, May 17, 3:30 PM + 3 more
12 Dudley Rd
Foraging Walk
Sat, May 17, 3:30 PM + 3 more
12 Dudley Rd
Sales end soon
Scavenger Hunt New Haven
Today at 2:00 PM + 61 more
New Haven
Sales end soon
Scavenger Hunt New Haven
Today at 2:00 PM + 61 more
New Haven

Trends in Pittsfield

Explore more trends

Frequently asked questions about Pittsfield

What are the best events to attend?

According to Eventbrite, the best events are:

CT Trails Day Hike

Trails Day Paddle - Wethersfield Cove

Keene Outdoor Craftfest & Classic Car Exhibition 2025

2025 Kids Fishing Derby

Which events are currently trending in Pittsfield?

The trending searches this month in Pittsfield are:

Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Scavenger Hunt Worcester

You Sleuth Augmented Reality Detective Experience

Scavenger Hunt New Haven

Easter Morning Wildflower Walk at Distant Hill Nature Trail

CT Trails Day Hike

CT Trails Day Hike

Trails Day Paddle - Wethersfield Cove

Trails Day Paddle - Wethersfield Cove

Keene Outdoor Craftfest & Classic Car Exhibition 2025

Keene Outdoor Craftfest & Classic Car Exhibition 2025

2025 Kids Fishing Derby

2025 Kids Fishing Derby

Monday Intermediate ride, Quillinan Reservoir

Monday Intermediate ride, Quillinan Reservoir

Scavenger Hunt Worcester

Scavenger Hunt Worcester

You Sleuth Augmented Reality Detective Experience

You Sleuth Augmented Reality Detective Experience

Moonlight Night Hike

Moonlight Night Hike

Guided Spring Bird Walk: Haddam Meadows State Park

Guided Spring Bird Walk: Haddam Meadows State Park

Easter Morning Wildflower Walk at Distant Hill Nature Trail

Easter Morning Wildflower Walk at Distant Hill Nature Trail

Easter Afternoon Wildflower Walk at Distant Hill Nature Trail

Easter Afternoon Wildflower Walk at Distant Hill Nature Trail

Distant Hill Pavilion Celebration with 'The Caterpillar Lab'

Distant Hill Pavilion Celebration with 'The Caterpillar Lab'

Insect Tracking Walk as part of our Pavilion Celebration at Distant Hill

Insect Tracking Walk as part of our Pavilion Celebration at Distant Hill

NEMBA Adventure Series - Pomfret Fun Ride

NEMBA Adventure Series - Pomfret Fun Ride

Summer Nature Days: Week of July 14th to 18th

Summer Nature Days: Week of July 14th to 18th

Summer Nature Days: Week of July 21st to 25th

Summer Nature Days: Week of July 21st to 25th

Summer Nature Days: Week of Aug. 4th to 8th

Summer Nature Days: Week of Aug. 4th to 8th

Summer Nature Days: Week of Aug. 11th to 15th

Summer Nature Days: Week of Aug. 11th to 15th

Foraging Walk

Foraging Walk

Scavenger Hunt New Haven

Scavenger Hunt New Haven

Things to do around Pittsfield

Trends in Pittsfield

1. Paint and sip

2. Easter brunch

3. Stand up comedy

4. Craft fairs

5. Music bingo berkshire

6. Live music

7. Speed dating

8. Protest

9. Open mic

10. Puppy yoga

11. Easter egg hunt

12. Bingo