Best events in
Windham

Looking for events or things to do in Windham, NY? The town's calendar is shaped by its mountain setting, with a lively après-ski scene in winter and outdoor festivals in warmer months. Days are often spent on the slopes or trails, while evenings bring a more social atmosphere to the cafes and pubs along Main Street.

Evenings along Main Street have a relaxed vibe, with locals and visitors gathering at spots like The Windham Local or Cave Mountain Brewing Company.
Windham Mountain Club is a central hub for activities, from recurring social golf events to major seasonal festivals.
The summer brings cultural performances to the area, including the annual Windham Chamber Music Festival.

autocomplete

Events near Windham

Explore more events

HUNTER MTN HORROR STORY

Tomorrow • 5:00 PM

Slopes Bar, Restaurant & Billiards

Check ticket price on event

Awaken Your Creativity: A 3 Day Transformative Art Retreat

Fri, Nov 6 • 6:00 PM

Chestnut Hill Farm

Check ticket price on event

Chillout Comedy Club at Mirabella’s: Live Stand-Up Comedy in Saugerties!!

Sat, Nov 7 • 8:00 PM

Mirabellas

Check ticket price on event

The Bones of J.R. Jones w/ Chris Kasper

Sat, Nov 14 • 7:00 PM

Colony

Check ticket price on event

Holiday Wreath Workshop with the Master Gardener Volunteers - Acra

Sat, Nov 21 • 9:30 AM

Agroforestry Resource Center

Check ticket price on event

CHERISH THE LADIES A CELTIC CHRISTMAS

Fri, Dec 18 • 7:00 PM

The Shamrock House

Check ticket price on event

New Year's Eve 2027 at Hotel Lilien: Annual Fireside Countdown

Thu, Dec 31 • 5:00 PM

Hotel Lilien

Check ticket price on event

Stained Glass Intensive with Erin Glassworks

Fri, Jan 22 • 1:00 PM

348 Sunside Rd

Check ticket price on event

HUNTER MTN HORROR STORY

Tomorrow • 5:00 PM

Slopes Bar, Restaurant & Billiards

Check ticket price on event

Awaken Your Creativity: A 3 Day Transformative Art Retreat

Fri, Nov 6 • 6:00 PM

Chestnut Hill Farm

Check ticket price on event

Chillout Comedy Club at Mirabella’s: Live Stand-Up Comedy in Saugerties!!

Sat, Nov 7 • 8:00 PM

Mirabellas

Check ticket price on event

The Bones of J.R. Jones w/ Chris Kasper

Sat, Nov 14 • 7:00 PM

Colony

Check ticket price on event

Holiday Wreath Workshop with the Master Gardener Volunteers - Acra

Sat, Nov 21 • 9:30 AM

Agroforestry Resource Center

Check ticket price on event

CHERISH THE LADIES A CELTIC CHRISTMAS

Fri, Dec 18 • 7:00 PM

The Shamrock House

Check ticket price on event

New Year's Eve 2027 at Hotel Lilien: Annual Fireside Countdown

Thu, Dec 31 • 5:00 PM

Hotel Lilien

Check ticket price on event

Stained Glass Intensive with Erin Glassworks

Fri, Jan 22 • 1:00 PM

348 Sunside Rd

Check ticket price on event

Explore more events

Nearby cities

Albany

34 miles away

Troy

40 miles away

Schenectady

38 miles away

Kingston

29 miles away

Woodstock

20 miles away

Poughkeepsie

45 miles away

Hudson

24 miles away

Rhinebeck

32 miles away

Claverack-Red Mills

28 miles away

Westmere

32 miles away

New Paltz

40 miles away

Menands

36 miles away

Kinderhook

28 miles away

Highland

44 miles away

Rosendale Hamlet

33 miles away

Lenox

49 miles away

Chatham

33 miles away

Oneonta

43 miles away

Crown Heights

49 miles away

Great Barrington

46 miles away

Ellenville

42 miles away

Saugerties

22 miles away

Walton

47 miles away

Amsterdam

42 miles away

Stone Ridge

33 miles away

Rotterdam

35 miles away

Lakeville

48 miles away

Tivoli

25 miles away

Red Hook

29 miles away

Millerton

45 miles away

Albany

34 miles away

Troy

40 miles away

Schenectady

38 miles away

Kingston

29 miles away

Woodstock

20 miles away

Poughkeepsie

45 miles away

Hudson

24 miles away

Rhinebeck

32 miles away

Claverack-Red Mills

28 miles away

Westmere

32 miles away

New Paltz

40 miles away

Menands

36 miles away

Kinderhook

28 miles away

Highland

44 miles away

Rosendale Hamlet

33 miles away

Lenox

49 miles away

Chatham

33 miles away

Oneonta

43 miles away

Crown Heights

49 miles away

Great Barrington

46 miles away

Ellenville

42 miles away

Saugerties

22 miles away

Walton

47 miles away

Amsterdam

42 miles away

Stone Ridge

33 miles away

Rotterdam

35 miles away

Lakeville

48 miles away

Tivoli

25 miles away

Red Hook

29 miles away

Millerton

45 miles away

Online Events

Explore more events

OUTSIDER ART: Drawing The Spirit World

Today • 6:30 PM GMT

Check ticket price on event

Humanitarian Water Engineering Fall 2026

Check ticket price on event

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

Thursday • 1:00 PM GMT

Check ticket price on event

Managing Your Emotions - Prof Ethan Kross

Tue, Nov 10 • 7:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

Check ticket price on event

OUTSIDER ART: Drawing The Spirit World

Today • 6:30 PM GMT

Check ticket price on event

Humanitarian Water Engineering Fall 2026

Check ticket price on event

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

Thursday • 1:00 PM GMT

Check ticket price on event

Managing Your Emotions - Prof Ethan Kross

Tue, Nov 10 • 7:00 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

REVISED Cottage Food Safety Statewide Online Training

Fri, Nov 13 • 9:00 AM MST

Check ticket price on event

The MI5 Archive: Official Secrets

Fri, Nov 27 • 2:00 PM GMT

Check ticket price on event

Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

Check ticket price on event

Explore more events

Frequently asked questions about Windham

Where can I find live music events in Windham?

Cave Mountain Brewing Company sometimes features live music. For classical and jazz performances, the annual Windham Chamber Music Festival is a highlight of the summer season, presenting a series of concerts.

What are some family-friendly things to do?

The Annual Autumn Affair is a great event for all ages. Held each Columbus Day weekend, this town-wide celebration includes local vendors, activities, and a festive atmosphere perfect for families.

Are there any free events to attend in Windham?

The Windham Farmers' Market is a free event to browse. Taking place on Main Street, it's an excellent way to see local and organic goods from regional artisans and farms every Saturday morning.

How can I experience the local food and drink scene?

Main Street is the best place to start your culinary tour. Grab a coffee at The Windham Local or enjoy a craft beer at Cave Mountain Brewing Company after a day of outdoor activities.

What is the nightlife like in Windham?

The nightlife is centered on a relaxed, social atmosphere. The pubs and restaurants along Main Street, such as The Windham Local, are popular spots for an evening drink, especially during the busy ski season.

Does Windham host large community events?

Yes, Windham hosts several signature community events throughout the year. The town comes together for the Annual Autumn Affair, while venues like The Centre Property on Main Street host various local gatherings.

What kind of outdoor events are available?

Windham Mountain Club offers year-round outdoor recreation. It is known for skiing and snowboarding in the winter, while the warmer months are popular for mountain biking, hiking, and golf events.

Where's a good spot for a date night?

A classic date night could start with dinner on Main Street. For something different, consider attending a performance during the Windham Chamber Music Festival for a memorable cultural event in the summer.

Events near Windham

HUNTER MTN HORROR STORY

Awaken Your Creativity: A 3 Day Transformative Art Retreat

Chillout Comedy Club at Mirabella’s: Live Stand-Up Comedy in Saugerties!!

The Bones of J.R. Jones w/ Chris Kasper

Holiday Wreath Workshop with the Master Gardener Volunteers - Acra

CHERISH THE LADIES A CELTIC CHRISTMAS

New Year's Eve 2027 at Hotel Lilien: Annual Fireside Countdown

Stained Glass Intensive with Erin Glassworks

HUNTER MTN HORROR STORY

Awaken Your Creativity: A 3 Day Transformative Art Retreat

Chillout Comedy Club at Mirabella’s: Live Stand-Up Comedy in Saugerties!!

The Bones of J.R. Jones w/ Chris Kasper

Holiday Wreath Workshop with the Master Gardener Volunteers - Acra

CHERISH THE LADIES A CELTIC CHRISTMAS

New Year's Eve 2027 at Hotel Lilien: Annual Fireside Countdown

Stained Glass Intensive with Erin Glassworks

Trending searches

1. Halloween

2. Music in windham ny

3. Windham

4. Sound bath

5. New years eve 2026 windham

6. Mushroom foraging

7. Mountain yoga

8. Goat yoga

9. Fall foliage

10. Fall activity

Nearby cities

Albany

Troy

Schenectady

Kingston

Woodstock

Poughkeepsie

Hudson

Rhinebeck

Claverack-Red Mills

Westmere

New Paltz

Menands

Kinderhook

Highland

Rosendale Hamlet

Lenox

Chatham

Oneonta

Crown Heights

Great Barrington

Ellenville

Saugerties

Walton

Amsterdam

Stone Ridge

Rotterdam

Lakeville

Tivoli

Red Hook

Millerton

Albany

Troy

Schenectady

Kingston

Woodstock

Poughkeepsie

Hudson

Rhinebeck

Claverack-Red Mills

Westmere

New Paltz

Menands

Kinderhook

Highland

Rosendale Hamlet

Lenox

Chatham

Oneonta

Crown Heights

Great Barrington

Ellenville