Festivals near Poughkeepsie, NY.

Middletown 2026 Summer Concert Series

• Jun. 26 - Jun 26, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Middletown 2026 Summer Concert Series

• Jul. 3 - Jul 3, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Summerfest Free Bubble Show

• Jul. 14 - Jul 14, 2026
• Litchfield Community Center - Litchfield, CT USA

• FREE!!

Bubbletastic Bubble Show with Charlie and the Bubble Factory All ages Watch in amazement as Charlie and the Bubble Factory transform soap and air in ....

Middletown 2026 Summer Concert Series

• Jul. 17 - Jul 17, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Uplift Festival & Retreat

• Jul. 24 - Jul 26, 2026
• 375 Pantherkill Rd - Phoenicia, NY USA

• Other / General

• $250+

This summer, Uplift Festival gathers a vibrant community at Menla Retreat & Dewa Spa for a joyful 3-day / 2-night immersive experience centered on mov ....

Middletown 2026 Summer Concert Series

• Jul. 24 - Jul 24, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Middletown 2026 Summer Concert Series

• Jul. 31 - Jul 31, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Middletown 2026 Summer Concert Series

• Aug. 7 - Aug 7, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Middletown 2026 Summer Concert Series

• Aug. 14 - Aug 14, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

15th Putnam County Wine & Music Fest

• Aug. 22 - Aug 23, 2026
• Putnam County Veterans Memorial Park - Carmel Hamlet, NY USA

• Music

• $10 - $25

Join us for the 15th Annual Putnam County Wine & Music Fest at Putnam County Veterans Memorial Park (Upper), 201 Gipsy Trail Road, Carmel, NY. The eve ....

Middletown 2026 Summer Concert Series

• Aug. 28 - Aug 28, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Honey Harvest Festival

• Aug. 30 - Aug 30, 2026
• Bartlett Arboretum & Gardens - Stamford, CT USA

• Arts (Arts & Crafts)
• Community (Community / Social)
• Community (Family & Kids)
• Music
• Seasonal (Fall)

• FREE!!

The Honey Harvest Festival serves as an essential educational platform to raise awareness about the significance of honeybees and pollinators in our e ....

Riverkeeper Fish Migration Celebration: Newburgh Welcoming of the Fish

• Jun. 20 - Jun 20, 2026
• Unico Park - Newburgh, NY USA

• Other / General

It’s free, family-friendly, and delightfully fishy! Celebrate the epic journeys of Hudson River fishes with a puppet performance by inspired artist Rh ....

Middletown 2026 Summer Concert Series

• Jun. 19 - Jun 19, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

PAWPAWPALOOZA 2026

• Jun. 13 - Jun 13, 2026
• 94 S Main St - Newtown, CT USA

Join us for our 5th Annual pet adoption and open house on Saturday, June 13th from 11AM–3PM at Pleasant Paws Pet Center in Newtown, CT! PAWPAWPALOOZA ....

Hudson Valley Fermentation Festival 2026

• Jun. 13 - Jun 14, 2026
• Twin Star Orchards - New Paltz, NY USA

• $1 - $10
• $10 - $25
• $25 - $50
• $50 - $100

Join us for the 2026 Hudson Valley Fermentation Festival, where you can explore a lively outdoor tasting market, packed with local producers of fermen ....

Middletown 2026 Summer Concert Series

• Jun. 12 - Jun 12, 2026
• John F. Degnan Square - Middletown, NY USA

• Music

Outdoor music returns this summer at John F. Degnan Square. Join us weekly for music from 7 PM to 9 PM! ....

Westchester Magazine Wine & Food Festival Returns

• Jun. 9 - Jun 14, 2026
• Westchester County - Westchester County, NY USA

• Food / Wine / Beer

• $50 - $100
• $100 - $250

For more than two decades, Westchester Magazine’s Wine & Food Festival has been a gathering place—where chefs, makers, and neighbors come together to ....

Westchester Magazine's Wine & Food Festival Returns

• Jun. 9 - Jun 14, 2026
• Westchester County - Westchester County, NY USA

• Food / Wine / Beer

• $50 - $100
• $100 - $250

For more than two decades, Westchester Magazine’s Wine & Food Festival has been a gathering place—where chefs, makers, and neighbors come together to ....

Music Mountains 97th Season Opening Benefit Concert & Reception Feat. Benjamin Hochman & Friends

• Jun. 7 - Jun 7, 2026
• 225 Music Mountain Rd - Canaan, CT USA

• Music

• $50 - $100

Benjamin Hochman & Friends from the Met Opera Benjamin Hochman, Piano Benjamin Bowman, Violin Milan Milisavljevic, Viola Joel Noyes, Cello Johann Seb ....

2026 Oxford Nature and Arts Festival

• Jun. 7 - Jun 7, 2026
• 486 Oxford Rd - Oxford, CT USA

• Other / General

On Sunday June 7, the Oxford Main Street Project Corporation will be hosting the 2026 Oxford Nature and Arts Festival. The festival will run Sunday m ....

Old Mill Singers Spring Concerts: A Tapestry of American Song

• Jun. 6 - Jun 7, 2026
• The Clearview School - Briarcliff Manor, NY USA

• Music

• $10 - $25

Immerse yourself in this fabulous musical encore of the past and the evolution of today’s American music. The Old Mill Singers will perform old time ....

Blue Rider Stables Summer Benefit

• Jun. 6 - Jun 6, 2026
• 15 Farm Ln - Great Barrington, MA USA

• Music

• $50 - $100

This annual event brings together supporters, families, riders and friends for an evening of equines, celebration, and live music, in support of Blue ....

Berkshire Bach Society presents MUSIK VOR BACH: 17th CENTURY FRENCH AIRS DE COUR

• Jun. 6 - Jun 6, 2026
• Unitarian Universalist Meeting of South Berkshire - Housatonic, MA USA

• Music

• $25 - $50

Berkshire Bach presents MUSIK VOR BACH: 17th century FRENCH AIRS DE COUR, a concert of early Baroque music featuring James Reese, tenor, and Brandon ....