Best events in
Lenox

Events and things to do in Lenox, MA, are deeply tied to the seasons and the town's rich cultural heritage. The area's legacy as a Gilded Age retreat underpins a lively arts scene, anchored by world-class music and theater. From bustling summer performances in the Berkshire Hills to cozy gatherings in the historic village center, the town offers a distinct rhythm throughout the year.

Explore historic Lenox Village, where boutique shops and galleries serve as the backdrop for seasonal Art Walks and the annual Lenox Apple Squeeze.
Experience world-class performances at Tanglewood, the celebrated summer home of the Boston Symphony Orchestra, or enjoy classic plays at Shakespeare & Company.
Attend intimate concerts and author talks hosted at historic estates like The Mount, Edith Wharton's Home, and Ventfort Hall Mansion.

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Events near Lenox

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The Berkshire Coven: A Sanderson Sisters Spectacle

Fri, Oct 16 • 7:30 PM

The Foundry West Stockbridge

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Q-MoB 50% Discount: Fresh Voices in Dance @ Jacobs Pillow (Becket, MA)

Fri, Oct 16 • 5:30 PM

Jacob's Pillow

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Gnocchi & Gnudi Hands-On: A Taste of Italy with Lee Davenport

Sat, Oct 17 • 11:00 AM

HGS Home Chef

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Hot Shot Hillbillies & Refrigerators at Woodlife

Sat, Oct 24 • 12:30 PM

36 Old Rte 20

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The House Remembers An Immersive Halloween Dinner at The Inn at Stockbridge

Fri, Oct 30 • 6:00 PM

The Inn at Stockbridge

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La Paulée Harvest Celebration

Sat, Oct 31 • 6:30 PM

The Aviary Kinderhook

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The Shining @ Holiday Inn

Sat, Oct 31 • 8:00 PM

Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Wisdom Lodge Harvest Night at Hill Top Orchards

Sat, Nov 21 • 5:30 PM

Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards

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The Berkshire Coven: A Sanderson Sisters Spectacle

Fri, Oct 16 • 7:30 PM

The Foundry West Stockbridge

Check ticket price on event

Q-MoB 50% Discount: Fresh Voices in Dance @ Jacobs Pillow (Becket, MA)

Fri, Oct 16 • 5:30 PM

Jacob's Pillow

Check ticket price on event

Gnocchi & Gnudi Hands-On: A Taste of Italy with Lee Davenport

Sat, Oct 17 • 11:00 AM

HGS Home Chef

Check ticket price on event

Hot Shot Hillbillies & Refrigerators at Woodlife

Sat, Oct 24 • 12:30 PM

36 Old Rte 20

Check ticket price on event

The House Remembers An Immersive Halloween Dinner at The Inn at Stockbridge

Fri, Oct 30 • 6:00 PM

The Inn at Stockbridge

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La Paulée Harvest Celebration

Sat, Oct 31 • 6:30 PM

The Aviary Kinderhook

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The Shining @ Holiday Inn

Sat, Oct 31 • 8:00 PM

Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Wisdom Lodge Harvest Night at Hill Top Orchards

Sat, Nov 21 • 5:30 PM

Hilltop Orchards Home of Furnace Brook Winery and Jmash Cidery and The Taproom at Hilltop Orchards

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Hudson

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Winsted

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Torrington

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Chicopee

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Menands

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West Springfield Town

37 miles away

Claverack-Red Mills

24 miles away

Bristol

50 miles away

Canton Valley

42 miles away

Windsor Locks

43 miles away

New Hartford Center

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New Britain

50 miles away

Rhinebeck

44 miles away

Online Events

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

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Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

Check ticket price on event

Coming Together for Multilingual Children with DLD

Thu, Oct 22 • 6:00 PM GMT+2

Check ticket price on event

Biodiversity Law and Governance Day 2026

Sat, Oct 24 • 11:30 AM GMT+4

Check ticket price on event

(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

Check ticket price on event

Witch hunts and real lives

Fri, Oct 30 • 2:00 PM GMT

Check ticket price on event

No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Frequently asked questions about Lenox

Where can I find live music events in Lenox?

Tanglewood is the premier destination for major summer concerts, from classical to contemporary music. For a different scale, look for free performance events in Lilac Park during the summer or intimate jazz sets hosted in downtown inns and restaurants.

What are the best art events in the area?

Downtown Lenox transforms into an open-air gallery during the annual Spring & Fall Art Walks. The Mount also hosts cultural programs, while its NightWood installation is a popular immersive sound and light event held annually in the winter.

Are there family-friendly events in Lenox?

Yes, the annual Lenox Apple Squeeze is a popular fall festival perfect for all ages. Other family-friendly events include picnicking on the lawn at Tanglewood and visiting the weekly Lenox Farmer's Market, which often features live music.

What kind of outdoor events does Lenox offer?

Many Lenox events take place outdoors, especially in the summer. The Tanglewood Music Festival features concerts in open-air sheds, Shakespeare & Company has an outdoor stage, and the Concerts in the Park series offers free shows in Lilac Park.

How can I find free events in Lenox?

Look for the Concerts in the Park series for free evening shows in Lilac Park during the summer. The seasonal Art Walks and the Lenox Farmer's Market are also free to attend, offering opportunities to browse local art and goods in the downtown village.

Do you have any recommendations for a date night in Lenox?

A classic Lenox date night pairs a pre-performance dinner downtown with a show at Tanglewood or Shakespeare & Company. For something unique, consider an author talk at The Mount or a concert at the historic Ventfort Hall Mansion.

Where are the food and drink events centered in Lenox?

Downtown Lenox is the hub for food-focused happenings like the annual Lenox Apple Squeeze. The weekly Lenox Farmer's Market also gathers local and regional food vendors, offering fresh produce and baked goods from late spring through early fall.

What's the event scene like in historic Lenox Village?

The walkable downtown village hosts many of the town's signature events. This area is the center for the Lenox Apple Squeeze and the seasonal Art Walks, with a charming atmosphere created by its galleries, shops, and historic buildings.

Events near Lenox

The Berkshire Coven: A Sanderson Sisters Spectacle

Q-MoB 50% Discount: Fresh Voices in Dance @ Jacobs Pillow (Becket, MA)

Gnocchi & Gnudi Hands-On: A Taste of Italy with Lee Davenport

Hot Shot Hillbillies & Refrigerators at Woodlife

The House Remembers An Immersive Halloween Dinner at The Inn at Stockbridge

La Paulée Harvest Celebration

The Shining @ Holiday Inn

Wisdom Lodge Harvest Night at Hill Top Orchards

The Berkshire Coven: A Sanderson Sisters Spectacle

Q-MoB 50% Discount: Fresh Voices in Dance @ Jacobs Pillow (Becket, MA)

Gnocchi & Gnudi Hands-On: A Taste of Italy with Lee Davenport

Hot Shot Hillbillies & Refrigerators at Woodlife

The House Remembers An Immersive Halloween Dinner at The Inn at Stockbridge

La Paulée Harvest Celebration

The Shining @ Holiday Inn

Wisdom Lodge Harvest Night at Hill Top Orchards

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Nearby cities

Albany

Troy

Springfield

Schenectady

Kingston

Woodstock

West Hartford

Tariffville

Holyoke

Westfield

Agawam Town

Northampton

Hudson

Winsted

Amherst Center

Torrington

Pittsfield

Easthampton Town

Hartford

North Amherst

Chicopee

Menands

West Springfield Town

Claverack-Red Mills

Bristol

Canton Valley

Windsor Locks

New Hartford Center

New Britain

Rhinebeck

Albany

Troy

Springfield

Schenectady

Kingston

Woodstock

West Hartford

Tariffville

Holyoke

Westfield

Agawam Town

Northampton

Hudson

Winsted

Amherst Center

Torrington

Pittsfield

Easthampton Town

Hartford