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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Events near Ashland

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The Understory Presents: Exploring Autumn's Abundance

Thursday • 4:00 PM

722 Sandy Plains Rd

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Family Constellations Community Circle · Greenville, NY

Wed, Oct 21 • 6:00 PM

Śaranam Center for Healing & Transformation

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This Place Is Special - Volume 2

Sat, Oct 24 • 10:00 AM

Prattsville Art Center & Residency & Phoenix Web Free Store

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Spellbound Supper + Amaro Magic

Sun, Oct 25 • 5:00 PM

Peekamoose Restaurant & Tap Room

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HUNTER MTN HORROR STORY

Sat, Oct 31 • 5:00 PM

Slopes Bar, Restaurant & Billiards

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John Splithoff

Fri, Nov 6 • 7:00 PM

Colony

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Wildlife Tracking with Daniel Hansche

Mon, Nov 9 • 9:00 AM

Siuslaw Model Forest - Cornell Cooperative Extension

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Fold Form Metalsmithing Intensive

Fri, Feb 12 • 1:00 PM

348 Sunside Rd

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The Understory Presents: Exploring Autumn's Abundance

Thursday • 4:00 PM

722 Sandy Plains Rd

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Family Constellations Community Circle · Greenville, NY

Wed, Oct 21 • 6:00 PM

Śaranam Center for Healing & Transformation

Check ticket price on event

This Place Is Special - Volume 2

Sat, Oct 24 • 10:00 AM

Prattsville Art Center & Residency & Phoenix Web Free Store

Check ticket price on event

Spellbound Supper + Amaro Magic

Sun, Oct 25 • 5:00 PM

Peekamoose Restaurant & Tap Room

Check ticket price on event

HUNTER MTN HORROR STORY

Sat, Oct 31 • 5:00 PM

Slopes Bar, Restaurant & Billiards

Check ticket price on event

John Splithoff

Fri, Nov 6 • 7:00 PM

Colony

Check ticket price on event

Wildlife Tracking with Daniel Hansche

Mon, Nov 9 • 9:00 AM

Siuslaw Model Forest - Cornell Cooperative Extension

Check ticket price on event

Fold Form Metalsmithing Intensive

Fri, Feb 12 • 1:00 PM

348 Sunside Rd

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Nearby cities

Albany

38 miles away

Troy

44 miles away

Kingston

31 miles away

Schenectady

41 miles away

Woodstock

21 miles away

Poughkeepsie

46 miles away

Hudson

28 miles away

Menands

40 miles away

Claverack-Red Mills

32 miles away

New Paltz

41 miles away

Rhinebeck

34 miles away

Kinderhook

33 miles away

Highland

45 miles away

Rosendale Hamlet

34 miles away

Rotterdam

39 miles away

Westmere

36 miles away

East Greenbush

38 miles away

Ellenville

41 miles away

Chatham

38 miles away

Catskill

24 miles away

Rensselaer

38 miles away

Hobart

18 miles away

Colonie

38 miles away

Cohoes

46 miles away

Amsterdam

44 miles away

Oneonta

39 miles away

Stone Ridge

33 miles away

Hurley

30 miles away

Kerhonkson

37 miles away

Saugerties

25 miles away

Albany

38 miles away

Troy

44 miles away

Kingston

31 miles away

Schenectady

41 miles away

Woodstock

21 miles away

Poughkeepsie

46 miles away

Hudson

28 miles away

Menands

40 miles away

Claverack-Red Mills

32 miles away

New Paltz

41 miles away

Rhinebeck

34 miles away

Kinderhook

33 miles away

Highland

45 miles away

Rosendale Hamlet

34 miles away

Rotterdam

39 miles away

Westmere

36 miles away

East Greenbush

38 miles away

Ellenville

41 miles away

Chatham

38 miles away

Catskill

24 miles away

Rensselaer

38 miles away

Hobart

18 miles away

Colonie

38 miles away

Cohoes

46 miles away

Amsterdam

44 miles away

Oneonta

39 miles away

Stone Ridge

33 miles away

Hurley

30 miles away

Kerhonkson

37 miles away

Saugerties

25 miles away

Online Events

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How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

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Perfectionnement en programmation Python [en ligne, PYT102]

Thursday • 9:00 AM EDT

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HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

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Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Saturday • 9:00 AM EDT

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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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How To Be Kind To Yourself - Shahroo Izadi

Wednesday • 7:00 PM GMT+1

Check ticket price on event

Perfectionnement en programmation Python [en ligne, PYT102]

Thursday • 9:00 AM EDT

Check ticket price on event

HBR Book Webinar: Resilient Optimism

Thursday • 1:00 PM GMT+1

Check ticket price on event

Today's RDH Virtual Dental Continuing Education (CE) Event - Oct. 17, 2026

Saturday • 9:00 AM EDT

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

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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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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.