Best events in
Ashland

For events and things to do in Ashland, NY, the local scene is defined by its Catskill Mountain setting and strong community spirit. Many gatherings are centered around Ashland Town Park, while the neighboring town of Windham offers a more bustling atmosphere with galleries and seasonal festivals. The area's character shifts with the seasons, from a lively ski town in winter to a hub for outdoor recreation and markets in the warmer months.

Start an outing on Windham's walkable Main Street, home to a seasonal farmers' market, the Annual Autumn Affair, and the contemporary Windham Fine Arts gallery.
Find family-friendly community gatherings at Ashland Town Park, the site for the Annual Antique Machinery Show and the Annual Cancer Patient Aid Car Show.
Experience classical music and cultural workshops in the nearby hamlet of Jewett at the Grazhda Music and Art Center, which hosts a Summer Concert Series.

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Nearby cities

Albany

38 miles away

Troy

44 miles away

Schenectady

41 miles away

Kingston

31 miles away

Woodstock

21 miles away

Poughkeepsie

46 miles away

Hudson

28 miles away

Rhinebeck

34 miles away

Claverack-Red Mills

32 miles away

New Paltz

41 miles away

Westmere

36 miles away

Saugerties

25 miles away

Chatham

38 miles away

Menands

40 miles away

Highland

45 miles away

Rosendale Hamlet

33 miles away

Kinderhook

33 miles away

Amsterdam

44 miles away

Ellenville

42 miles away

Walton

42 miles away

Cohoes

46 miles away

Oneonta

39 miles away

Stone Ridge

33 miles away

Tivoli

27 miles away

Red Hook

32 miles away

Millerton

49 miles away

Catskill

24 miles away

Hobart

18 miles away

Watervliet

44 miles away

Gardiner

44 miles away

Albany

38 miles away

Troy

44 miles away

Schenectady

41 miles away

Kingston

31 miles away

Woodstock

21 miles away

Poughkeepsie

46 miles away

Hudson

28 miles away

Rhinebeck

34 miles away

Claverack-Red Mills

32 miles away

New Paltz

41 miles away

Westmere

36 miles away

Saugerties

25 miles away

Chatham

38 miles away

Menands

40 miles away

Highland

45 miles away

Rosendale Hamlet

33 miles away

Kinderhook

33 miles away

Amsterdam

44 miles away

Ellenville

42 miles away

Walton

42 miles away

Cohoes

46 miles away

Oneonta

39 miles away

Stone Ridge

33 miles away

Tivoli

27 miles away

Red Hook

32 miles away

Millerton

49 miles away

Catskill

24 miles away

Hobart

18 miles away

Watervliet

44 miles away

Gardiner

44 miles away

Online Events

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

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I sì che aiutano a crescere. Essere genitori nell'epoca dell'IA

Monday • 9:00 PM GMT+1

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Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

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This Little World: a New History of Tudor and Stuart England

Wed, Nov 11 • 7:30 PM GMT

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Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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How to Choose a (New) Career Fast

Thu, Dec 3 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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The World of Bunny vs Monkey Workshop with Jamie Smart

Saturday • 10:00 AM GMT

Check ticket price on event

I sì che aiutano a crescere. Essere genitori nell'epoca dell'IA

Monday • 9:00 PM GMT+1

Check ticket price on event

Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

Check ticket price on event

This Little World: a New History of Tudor and Stuart England

Wed, Nov 11 • 7:30 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thu, Nov 12 • 2:00 PM UTC

Check ticket price on event

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

Check ticket price on event

How to Choose a (New) Career Fast

Thu, Dec 3 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Events near Ashland

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

Sat, Nov 14 • 7:00 PM

Colony

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Holiday Wreath Workshop with the Master Gardener Volunteers - Acra

Sat, Nov 21 • 9:30 AM

Agroforestry Resource Center

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CHERISH THE LADIES A CELTIC CHRISTMAS

Fri, Dec 18 • 7:00 PM

The Shamrock House

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Warren Miller Day's Off

Tue, Dec 29 • 7:00 PM

Union Grove Distillery

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

Thu, Dec 31 • 5:00 PM

Hotel Lilien

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Stained Glass Intensive with Erin Glassworks

Fri, Jan 22 • 1:00 PM

348 Sunside Rd

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Citech Winter Music Festival

Fri, Jan 22 • 8:00 PM

Slopes Bar, Restaurant & Billiards

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Forest & Flow Catskills Retreat

Fri, Apr 16 • 5:00 PM

The Maeve House

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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

Warren Miller Day's Off

Tue, Dec 29 • 7:00 PM

Union Grove Distillery

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

Citech Winter Music Festival

Fri, Jan 22 • 8:00 PM

Slopes Bar, Restaurant & Billiards

Check ticket price on event

Forest & Flow Catskills Retreat

Fri, Apr 16 • 5:00 PM

The Maeve House

Check ticket price on event

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Frequently asked questions about Ashland

Are there any art events in the Ashland area?

Windham Fine Arts is a key destination for gallery openings and receptions. The gallery showcases contemporary work from various artists and hosts Art Receptions to launch new exhibitions. Nearby, the Grazhda Music and Art Center in Jewett offers workshops on Ukrainian folk arts during the summer.

Where can I find live music events near Ashland?

The Grazhda Music and Art Center in Jewett hosts a Summer Concert Series. This classical music series takes place on Saturday evenings in July and August. Live music can also be found at seasonal events like the Windham Farmers' Market and the Annual Autumn Affair in Windham.

What are some family-friendly things to do in Ashland?

Ashland Town Park is the center for many local community events. The park hosts the Annual Antique Machinery Show and the Annual Cancer Patient Aid Car Show. It also features a playground, dog park, and plenty of open space for recreation.

What food and drink events are popular in the Ashland and Windham area?

The Vineyard at Windham offers wine tastings in its weekend tasting room. For local produce and artisanal goods, the Windham Farmers' Market is a popular gathering. Seasonal festivals, like Windham's Annual Autumn Affair, also feature local food vendors and an enjoyable atmosphere.

What are some popular outdoor events around Ashland?

The region's calendar is full of outdoor community gatherings and festivals. Ashland Town Park hosts several annual shows, and Windham's Main Street is home to the Annual Autumn Affair. The Windham Farmers' Market is another popular weekly outdoor event during its season.

Any date night ideas in the Ashland and Windham area?

A trip to The Vineyard at Windham makes for a memorable date. The boutique winery offers wine tastings on weekends in a scenic setting. For an artistic outing, consider an exhibition opening at Windham Fine Arts, which often features live music and a social atmosphere.

What's the difference between the event scenes in Ashland and Windham?

Ashland's events are focused on small-town community gatherings at the town park. Windham has a more bustling, visitor-oriented scene with a walkable Main Street that features galleries, a farmers' market, and festivals, especially on weekends when tourism is highest.

How can I find free things to do near Ashland?

Many community events in the area are free for the public to attend. Exploring the Windham Farmers' Market or attending an art reception at Windham Fine Arts are great ways to enjoy the local culture. Strolling through annual festivals on Windham's Main Street is another popular option.