Travel & outdoor events in Chestertown, NY

Search for something you love or check out popular events in your area.

2025 Christmas Dec 25-28 Killington $459 (3 Nights + Transport)
Thu, Dec 25, 4:00 PM
Vermont · Killington Resort
2025 Christmas Dec 25-28 Killington $459 (3 Nights + Transport)
Thu, Dec 25, 4:00 PM
Vermont · Killington Resort
2026 New Year Jan 1-4 Killington & Sugarbush $469 (3 Nights + Transport)
Thu, Jan 1, 4:00 PM
Vermont · Killington Resort
2026 New Year Jan 1-4 Killington & Sugarbush $469 (3 Nights + Transport)
Thu, Jan 1, 4:00 PM
Vermont · Killington Resort
Bus Trip to Salem, Mass. with Brown Coach
Sat, Oct 18, 6:30 AM
Johnstown · The Arc Lexington
Bus Trip to Salem, Mass. with Brown Coach
Sat, Oct 18, 6:30 AM
Johnstown · The Arc Lexington
Sales end soon
Adventurous Scavenger Hunt! - Saranac Lake‘s Spectacular Scavenger Soiree
Today at 8:00 AM + 207 more
Trudeau · 60 Main St
Sales end soon
Adventurous Scavenger Hunt! - Saranac Lake‘s Spectacular Scavenger Soiree
Today at 8:00 AM + 207 more
Trudeau · 60 Main St
Selling quickly
Bus Trip to New York City with Brown Coach
Sat, Dec 13, 6:30 AM
Johnstown · 465 N Perry St
Selling quickly
Bus Trip to New York City with Brown Coach
Sat, Dec 13, 6:30 AM
Johnstown · 465 N Perry St
Sales end soon
Amazing Scavenger Hunt! - Amsterdam‘s Alluring Adventure Hunt
Today at 8:00 AM + 213 more
South Amsterdam · 61 Church St
Sales end soon
Amazing Scavenger Hunt! - Amsterdam‘s Alluring Adventure Hunt
Today at 8:00 AM + 213 more
South Amsterdam · 61 Church St
Dec 19-21 Stratton $319 (2 Nights + Transport) Depart Queens NYC NJ
Fri, Dec 19, 4:00 PM
Vermont · Sugarbush Ski Resort
Dec 19-21 Stratton $319 (2 Nights + Transport) Depart Queens NYC NJ
Fri, Dec 19, 4:00 PM
Vermont · Sugarbush Ski Resort
2026 MLK Jan 16-19 Okemo $459 (3 Nights + Transport) Depart QNS NYC NJ
Fri, Jan 16, 4:00 PM
Vermont · Okemo Mountain Resort
2026 MLK Jan 16-19 Okemo $459 (3 Nights + Transport) Depart QNS NYC NJ
Fri, Jan 16, 4:00 PM
Vermont · Okemo Mountain Resort
Sales end soon
House & Garden Tour at the Shelburne Farms Inn 2025
Sunday at 1:30 PM + 20 more
Vermont · Shelburne Farms Inn
Sales end soon
House & Garden Tour at the Shelburne Farms Inn 2025
Sunday at 1:30 PM + 20 more
Vermont · Shelburne Farms Inn
Shelburne Farms Tour 2025
Today at 11:00 AM + 38 more
Vermont · 1611 Harbor Rd
Shelburne Farms Tour 2025
Today at 11:00 AM + 38 more
Vermont · 1611 Harbor Rd
Dec 12-14 Sugarbush $329 (2 Nights + Transport) Depart Queens NYC NJ
Fri, Dec 12, 4:00 PM
Vermont · Sugarbush Ski Resort
Dec 12-14 Sugarbush $329 (2 Nights + Transport) Depart Queens NYC NJ
Fri, Dec 12, 4:00 PM
Vermont · Sugarbush Ski Resort
Sales end soon
Adventurous Scavenger Hunt - Schenectady Shenanigans Scavenger Hunt
Today at 8:00 AM + 174 more
Mount Pleasant · 105 Jay St
Sales end soon
Adventurous Scavenger Hunt - Schenectady Shenanigans Scavenger Hunt
Today at 8:00 AM + 174 more
Mount Pleasant · 105 Jay St
Abenaki Campfire With Chief Don Stevens
Sun, Oct 5, 5:30 PM
Vermont · Farm Barn, Shelburne Farms
Abenaki Campfire With Chief Don Stevens
Sun, Oct 5, 5:30 PM
Vermont · Farm Barn, Shelburne Farms
Good Night, Farmyard
Wed, Oct 8, 5:45 PM
Vermont · Shelburne Farms
Good Night, Farmyard
Wed, Oct 8, 5:45 PM
Vermont · Shelburne Farms
Orienteering
Sat, Oct 25, 9:00 AM
Vermont · McClure Education Center in the Farm Barn, Shelburne Farms
Orienteering
Sat, Oct 25, 9:00 AM
Vermont · McClure Education Center in the Farm Barn, Shelburne Farms
Sales end soon
Schenectady Audio Tour: Echoes of Innovation and Historic Streets
Mount Pleasant · H. S. Barney Building
Sales end soon
Schenectady Audio Tour: Echoes of Innovation and Historic Streets
Mount Pleasant · H. S. Barney Building
Sales end soon
Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington
Today at 8:00 AM + 139 more
Old Bennington · Monument Square
Sales end soon
Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington
Today at 8:00 AM + 139 more
Old Bennington · Monument Square
Sales end soon
A Date Night Adventure! - Cohoes Scavenger Hunt
Tomorrow at 8:00 AM + 247 more
Crescent Station · 301 N Mohawk St
Sales end soon
A Date Night Adventure! - Cohoes Scavenger Hunt
Tomorrow at 8:00 AM + 247 more
Crescent Station · 301 N Mohawk St
Bennington Bash Scavenger Hunt
Today at 11:00 AM + 191 more
Bennington · The Coffee Bar
Bennington Bash Scavenger Hunt
Today at 11:00 AM + 191 more
Bennington · The Coffee Bar
Bennington Bash Amazing Race & Tour
Today at 11:00 AM + 191 more
Bennington · The Coffee Bar
Bennington Bash Amazing Race & Tour
Today at 11:00 AM + 191 more
Bennington · The Coffee Bar

Trends in Chestertown

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Frequently asked questions about Chestertown

What are the best events to attend?

According to Eventbrite, the best events are:

2025 Christmas Dec 25-28 Killington $459 (3 Nights + Transport)

2026 New Year Jan 1-4 Killington & Sugarbush $469 (3 Nights + Transport)

Bus Trip to Salem, Mass. with Brown Coach

Bus Trip to New York City with Brown Coach

Which events are currently trending in Chestertown?

The trending searches this month in Chestertown are:

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Which events are coming up?

Discover the best events happening soon – you don't want to miss them:

Adventurous Scavenger Hunt! - Saranac Lake‘s Spectacular Scavenger Soiree

Amazing Scavenger Hunt! - Amsterdam‘s Alluring Adventure Hunt

Adventurous Scavenger Hunt - Schenectady Shenanigans Scavenger Hunt

Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington

2025 Christmas Dec 25-28 Killington $459 (3 Nights + Transport)

2025 Christmas Dec 25-28 Killington $459 (3 Nights + Transport)

2026 New Year Jan 1-4 Killington & Sugarbush $469 (3 Nights + Transport)

2026 New Year Jan 1-4 Killington & Sugarbush $469 (3 Nights + Transport)

Bus Trip to Salem, Mass. with Brown Coach

Bus Trip to Salem, Mass. with Brown Coach

Adventurous Scavenger Hunt! - Saranac Lake‘s Spectacular Scavenger Soiree

Adventurous Scavenger Hunt! - Saranac Lake‘s Spectacular Scavenger Soiree

Bus Trip to New York City with Brown Coach

Bus Trip to New York City with Brown Coach

Amazing Scavenger Hunt! - Amsterdam‘s Alluring Adventure Hunt

Amazing Scavenger Hunt! - Amsterdam‘s Alluring Adventure Hunt

Dec 19-21 Stratton $319 (2 Nights + Transport) Depart Queens NYC NJ

Dec 19-21 Stratton $319 (2 Nights + Transport) Depart Queens NYC NJ

2026 MLK Jan 16-19 Okemo $459 (3 Nights + Transport) Depart QNS NYC NJ

2026 MLK Jan 16-19 Okemo $459 (3 Nights + Transport) Depart QNS NYC NJ

House & Garden Tour at the Shelburne Farms Inn 2025

House & Garden Tour at the Shelburne Farms Inn 2025

Shelburne Farms Tour 2025

Shelburne Farms Tour 2025

Dec 12-14 Sugarbush $329 (2 Nights + Transport) Depart Queens NYC NJ

Dec 12-14 Sugarbush $329 (2 Nights + Transport) Depart Queens NYC NJ

Adventurous Scavenger Hunt - Schenectady Shenanigans Scavenger Hunt

Adventurous Scavenger Hunt - Schenectady Shenanigans Scavenger Hunt

Abenaki Campfire With Chief Don Stevens

Abenaki Campfire With Chief Don Stevens

Good Night, Farmyard

Good Night, Farmyard

Orienteering

Orienteering

Schenectady Audio Tour: Echoes of Innovation and Historic Streets

Schenectady Audio Tour: Echoes of Innovation and Historic Streets

Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington

Awesome Scavenger Hunt! - The Revolutionary Ways of Bennington

A Date Night Adventure! - Cohoes Scavenger Hunt

A Date Night Adventure! - Cohoes Scavenger Hunt

Bennington Bash Scavenger Hunt

Bennington Bash Scavenger Hunt

Bennington Bash Amazing Race & Tour

Bennington Bash Amazing Race & Tour

Things to do around Chestertown

Trends in Chestertown

1. Stars above