Embark on a Chester New York scavenger hunt adventure through the heart of Orange County Treasure. Explore downtown, solve riddles, and tackle fun challenges as you uncover hidden gems like the Revolutionary Militia Plaque and 1915 Chester Depot. This interactive walking tour is flexible, competitive, and perfect for sightseeing with friends.
This scavenger hunt will help you explore Chester. This top rated Chester New York Scavenger Hunt scavenger hunt is 1.61 miles and has 7 stops.
5.0 (22 reviews)
Chester, nestled in the Hudson Valley Hideaway, offers a unique blend of history and charm. On this scavaHunt in Chester's city center, discover landmarks like Yelverton Store and World War I Monument while solving missions. Locals and visitors alike will love exploring this Appalachian Gateway—perfect for learning quirky local facts!
You can do our interactive scavenger hunt at any time.
Peer at the columns of this 1841 store, an Orange County Gem. Locals note that counting it's original stone steps makes for a fun photo challenge! Feel centuries of city center life pulse here.
At this outdoor activity stop, read the inscription and imagine musket drills echoing through time. Locals say the original militia captain's name appears only at sunset—can you find it on your Chester New York Scavenger Hunt?
Locals say you might hear echoes of an old bell on quiet mornings here. Capture it's architecture—perhaps your team will sense Chester's city center pulse during this guided tour stop.
Spot original rail tracks outside! Locals recall when onions from Black Dirt Region first rolled to NYC here. Can your team guess when the last train left during your Chester New York Scavenger Hunt mission?
Gather for a group selfie at Hambletonian's resting place. Local lore claims a lucky pat on the fence brings good fortune for your next puzzle. Will you test it during your Chester New York Scavenger Hunt?
Pause by this tribute—locals say it's time capsule holds surprises from Sugar Loaf Arts Village. Will you guess what is inside during your Chester New York Scavenger Hunt challenges?
Explore the historic tavern where legends like George Washington once mingled. Locals whisper of secrets hidden in the brickwork. Can your team uncover the oldest stone during this Chester New York Scavenger Hunt?
Grab your phone and some free time for a Chester New York Scavenger Hunt! Use our app to solve riddles, complete photo challenges, and explore iconic spots like Yelverton Inn. Earn points as you compete on the leaderboard while discovering hidden gems in this Historic Rail Village.
Activity Type: Anytime Scavenger Hunt
Starting Area: 104 Main St, Chester, NY 10918, USA
Travel Method: Walking
Walking Distance: 1.61 Mi (2.59 KM)
Time:1.5 - 2 Hours
Skill Level:Friend & Family Fun
Extra Admissions: None
Chester New York Scavenger Hunt Team Building Scavenger Hunts
Engage with your team by going spot to spot on an epic team building scavenger hunt!
Chester New York Scavenger Hunt Date Night Scavenger Hunt
Explore the most romantic spots of Chester on a Date Night Scavenger Hunt!
Chester New York Scavenger Hunt Bachelorette Scavenger Hunt
Challenges created to bring the bride's squad closer and make the celebration even more unforgettable
Chester New York Scavenger Hunt Birthday Scavenger Hunt
Celebrate with a birthday party scavenger hunt!
Love competition? On your Chester New York Scavenger Hunt, each player will tackle interactive challenges at spots like Hambletonian. Work together to solve riddles and trivia for a chance to top the leaderboard—and earn ultimate bragging rights!
Team: Max Power
Team: For the Lolz
Team: 1st not Last
Do you have what it takes to be a Chester New York Scavenger Hunt champion?
Exploring Downtown was thrilling! Loved visiting spots like Chester Village Hall while solving riddles. ScavengerHunt.com made it super engaging for tourists like us.
Lucas Wright
A fun way to discover Downtown Chester. From Yelverton Store to Revolutionary Militia Plaque, this scavenger hunt was packed with interesting history and challenges.
Amelia Clark
What an adventure in Chesterville! Great outdoor activity exploring the World War I Monument. A must-do if you're visiting the area, especially on sunny days.
Liam Morris
Perfect date idea in Chester's heart. Solving puzzles at Hambletonian and stopping by local spots made our day unforgettable. Highly recommend for couples.
Sophie Green
Had a blast exploring Chester's downtown! The scavenger hunt was the perfect mix of fun and learning. Loved seeing 1915 Chester Depot and the Yelverton Inn.
Ethan Brooks
Chester's downtown has so much history! The 1915 Depot visit during our scavenger hunt was a highlight of our tourist experience.
Noah Williams
If you're looking for fun things to do in Downtown, this scavenger hunt is a must. We uncovered hidden gems around Yelverton Inn and Store.
Mia Evans
Loved this family-friendly activity in Chester. Discovering spots like the Hambletonian statue made it exciting for both kids and adults.
Ava Johnson
The Downtown hunt is a perfect date idea. We solved puzzles and discovered the Revolutionary Militia Plaque, making it memorable.
Lucas Adams
Exploring Chester through the scavenger hunt was a delightful adventure. The World War I Monument & Time Capsule were fascinating highlights.
Emma Stone
As tourists, we found Chester one of a kind with this scavenger hunt. Seeing points of interest like the World War I Monument was simply awesome!
Liam Johnson
I loved discovering Downtown Chester with this hunt! From Yelverton Store to the Village Hall, it's a great way to see iconic landmarks.
Henry Perez
The Chester Scavenger Hunt is an amazing outdoor activity. Walking through downtown, we uncovered treasures like the Revolutionary Militia Plaque.
Sophia Nguyen
Had a fantastic date exploring Downtown Chester on the scavenger hunt. Solving puzzles at spots like 1915 Depot made it a memorable adventure!
George Thompson
Exploring Chester's hidden gems like the Yelverton Inn and Hambletonian was a blast! The Chester Scavenger Hunt is perfect for families, blending history and fun.
Evelyn Martinez
Chester Scavenger Hunt is an adventurous way to uncover local history. Exploring hidden gems like Bicentennial Time Capsule was fantastic for tourists!
Sophie Nguyen
Discovering Downtown Chester was a joy with this hunt. The Village Hall and Yelverton Store were highlights that made our walking tour memorable.
Kayla Fernandez
A fun outdoor activity exploring Downtown Chester's iconic spots, like the 1915 Depot and Hambletonian. Perfect way to see the city center.
Logan Patel
This was a perfect date idea in Downtown Chester. We bonded over the challenges at places like the World War I Monument and enjoyed every moment.
Ethan Morris
Exploring Chester on this scavenger hunt was a blast for our family. We loved solving puzzles around the Revolutionary Militia Plaque and Yelverton Inn.
Darla Thompson
© 2016-2025 Let's Roam, LLC. Let’s Roam® is a registered trademark. All Rights Reserved.
/-74.27761841,41.35609055,11/450x500?access_token=pk.eyJ1IjoibWZoYXJkaW5nIiwiYSI6ImNqbGlicnQ2MzBkeDgzcm9lbnQxb2dhNGoifQ.oWHnl0D4-eSNX-43SHqK8A&)
_Fort Worth_Texas_4ab5174c_large.jpeg)
