Chestertown, NY, is a charming little town nestled in the heart of the Adirondacks. With its beautiful mountains, peaceful lakes, and friendly community, it’s a perfect place for a day of fun. Whether you’re looking for outdoor adventures, cozy spots to relax, or a taste of local culture, Chestertown has something for everyone.
Today, we’ll share some exciting activities to enjoy in Chestertown. From hiking scenic trails to enjoying lakeside picnics, there are plenty of ways to connect with nature and make lasting memories. Get ready for a fun-filled adventure in this lovely town!
Things To Do In Chestertown Ny
1. Explore the Picturesque Chestertown Village Park for a Relaxing Picnic
Chestertown Village Park is a hidden gem in the heart of the town. Its lush greenery creates a perfect backdrop for a leisurely picnic. Visitors can find plenty of shaded spots to spread out their blankets and enjoy a meal under the trees.
The park features picnic tables and benches for those who prefer to sit and relax. Kids can enjoy the playground, making it a great spot for families. The nearby walking paths offer a charming way to explore the area after a meal.
For those who enjoy wildlife, keep an eye out for various birds and butterflies fluttering around the park. Spending time in this serene setting gives a lovely taste of nature while still being close to town.
In the summer, the park often hosts local events and activities that enhance its charm. It’s a lively place for community gatherings, concerts, and festivals.
Bringing a picnic to Chestertown Village Park is a delightful way to enjoy the outdoors. It’s a simple and enjoyable experience for everyone.
Address: 6405 NY-9, Chestertown, NY 12817.
2. Visit the Chester Historical Society Museum to Learn About Local History
The Chester Historical Society Museum is a fascinating spot for history buffs and curious visitors. This small but informative museum details the rich heritage of Chester and its surrounding areas. Each exhibit tells a unique story about the town’s past.
Visitors can view historical artifacts, photographs, and documents that showcase the community’s evolution. Knowledgeable staff are available to answer questions and provide deeper insights into each display. It’s like stepping back in time!
The museum regularly hosts special events, including guest speakers and themed exhibits, keeping the experience fresh and engaging. There’s always something new to learn about Chester’s history.
Families will find plenty to enjoy here as well. The museum nurtures a sense of community and pride, which resonates through its exhibits. It’s a great way to connect with the local culture.
A trip to the Chester Historical Society Museum is not just educational; it’s also an enjoyable way to appreciate the town’s history.
Address: 6047 NY-9, Chestertown, NY 12817.
3. Take a Scenic Hike on the Nearby Chester Challenge Trail
The Chester Challenge Trail offers a top-notch hiking experience for outdoor lovers. This scenic trail winds through beautiful forests and provides stunning views of the surrounding mountains and lakes. It’s suitable for both casual hikers and seasoned adventurers.
You can choose from several trail segments, each with varying levels of difficulty. As you hike, watch for the diverse wildlife that calls this area home. Birds, deer, and other creatures may be spotted along the way, making it an exciting adventure.
Each season brings a new beauty to the trail. In spring, vibrant wildflowers bloom; fall showcases stunning foliage colors. The trail is well-marked, which makes navigation easy.
Don’t forget to bring water and snacks! Pausing to enjoy a snack while soaking in the picturesque scenery is one of the highlights. Additionally, the trailhead features maps and information about the area.
A hike on the Chester Challenge Trail is an invigorating way to connect with nature and enjoy fresh air. It’s a must-visit for anyone in the area!
Address: 6359 NY-9, Chestertown, NY 12817.
4. Enjoy Fishing on the Schroon River That Runs Through Chestertown
Fishing enthusiasts will find plenty to love about the Schroon River in Chestertown. The river is well-known for its abundant fish populations, including trout and bass. Anglers can often be seen enjoying the peaceful waters as they cast their lines.
Finding a good fishing spot is easy thanks to the accessible banks along the river. Bring your gear and enjoy a relaxing day surrounded by nature. The calming sounds of flowing water and chirping birds add to the experience.
Local bait shops offer supplies and information about current fishing conditions. Whether you’re a beginner or a seasoned angler, the Schroon River has something for everyone. Many also appreciate the scenic views the river provides.
Families can make it a fun outing, teaching kids how to fish while enjoying quality time outdoors. Sharing stories and laughter by the river makes for wonderful memories.
Fishing on the Schroon River adds a rewarding touch to any trip to Chestertown. It’s a delightful way to embrace nature and tranquil surroundings.
Address: 6401 NY-9, Chestertown, NY 12817.
5. Spend a Day Kayaking or Canoeing on Lake George
Lake George is a perfect destination for kayaking and canoeing enthusiasts. The lake’s crystal-clear waters are inviting, making it a popular spot for paddlers of all skill levels. Kayaking offers a unique chance to explore the serene shoreline and hidden coves.
You can rent kayaks or canoes from nearby facilities if you don’t have your own. Many rental services also provide guided tours for those who prefer a little more direction. Experienced guides share local knowledge and discover hidden gems around the lake.
While paddling, keep an eye out for beautiful wildlife, including various bird species and playful otters. The lake’s stunning scenery provides a perfect backdrop for a day out on the water.
After an exhilarating day of paddling, take some time to relax along the shore. Picnic areas and beaches allow you to soak in the sun and enjoy a meal while admiring the view.
Canoeing or kayaking on Lake George is a fantastic way to experience the natural beauty of the area. It’s an adventure waiting to be enjoyed!
Address: 3D 6, 8, 4, 6, 6130 Lakeshore Dr, Lake George, NY 12845.
6. Attend Summertime Concerts at the Chestertown Farmer’s Market
The Chestertown Farmer’s Market is a vibrant community hub, especially during the summer months. Every week, local farmers and artisans gather to showcase fresh produce, handmade crafts, and delicious baked goods. It’s an ideal spot to support local vendors!
What makes the market truly special are the summertime concerts held in conjunction. Local musicians offer live performances that fill the air with delightful tunes, transforming the market into a lively festival atmosphere.
Families can explore the market, sample local delicacies, and groove to the music. Children can enjoy activities, making it a fun experience for everyone. The friendly atmosphere encourages community connection and engagement.
Don’t forget to grab some fresh fruits or flowers to take home! The market is a fantastic place to find specialty items and chat with friendly locals.
Attending concerts at the Chestertown Farmer’s Market is more than just shopping; it’s a celebration of community spirit. Enjoy an evening filled with music, laughter, and fresh food.
Address: 6050 NY-9, Chestertown, NY 12817.
7. Discover Local Art at the Loon Lake Arts and Crafts Festival
The Loon Lake Arts and Crafts Festival is an annual event that showcases the incredible talent of local artisans. When you attend this festival, you’ll find a plethora of handmade crafts, stunning artworks, and unique gifts. It’s an exceptional opportunity to connect with local creativity.
Visitors can stroll through rows of booths and meet the artists behind the creations. Many artisans are passionate about their craft and enjoy sharing their stories, making the experience even more special.
The festival often features live demonstrations, where attendees can see artisans at work. It’s not only entertaining but also educational, as you might learn something new about various crafts.
Along with beautiful crafts, festival-goers can enjoy delicious food from local vendors. Treat yourself to a snack while browsing the artistry around you. You’ll find everything from tasty baked goods to savory meals.
A visit to the Loon Lake Arts and Crafts Festival is a delightful way to celebrate local talent and creativity. It’s fun for art lovers and families alike!
Address: Loon Lake, Chestertown, NY 12817.
8. Visit the Riverside Gallery to View Works by Local Artists
The Riverside Gallery is a charming space that hosts works by local artists. This cozy gallery displays a variety of artwork, from stunning paintings to intricate pottery. It’s a great place for art enthusiasts and those new to the art scene alike!
Every visit provides the chance to discover different artists and their unique styles. The gallery often changes exhibitions, so there’s always something new to experience. You may even stumble upon your next favorite piece!
The supportive atmosphere encourages interaction, allowing artists to connect with visitors. Many artists share the inspiration behind their work, making the visit deeply engaging and personal.
In addition to viewing art, visitors can also purchase items. Buying local art is a fantastic way to support the community while acquiring a beautiful piece for your home.
Visiting the Riverside Gallery offers a rich cultural experience. It’s a wonderful blend of creativity, community, and artistic exploration.
Address: 6754 NY-9, Chestertown, NY 12817.
9. Go Horseback Riding at a Local Equestrian Center
Horseback riding in Chestertown is a relaxing and enjoyable way to explore the natural beauty of the region. Local equestrian centers offer guided rides suitable for all experience levels, making it fun for everyone. Whether you’re a beginner or an experienced rider, there’s something for you.
As you ride, you’ll journey through picturesque trails lined with trees and wildflowers. The fresh air and beautiful surroundings create a magical experience. Many trails wind through scenic forests and offer stunning views of the nearby lakes.
Experienced guides ensure safety while providing insights about the landscape and wildlife. You’ll likely learn interesting facts about the area during your ride.
Don’t worry if you’ve never ridden before. Riding lessons are often available for beginners, allowing you to build confidence in the saddle. It’s a great way to bond with these beautiful animals and study their behavior.
Horseback riding is a fantastic outdoor activity in Chestertown. It’s a memorable way to connect with nature while enjoying the thrill of riding.
Address: 4 Sutherland Rd, Chestertown, NY 12817.
10. Take a Scenic Drive Along the Adirondack Northway
The Adirondack Northway offers one of the most breathtaking drives in New York. Scenic views accompany you as you travel, with rolling hills, majestic mountains, and sparkling lakes at every turn. It’s a perfect day trip for anyone who enjoys stunning landscapes.
Along the way, there are plenty of opportunities to pull over and take pictures. Designated scenic overlooks allow you to stop and truly appreciate the beauty around you. Each season reveals a new charm, from lush greens in summer to vibrant autumn leaves.
Many visitors like to explore nearby hiking trails or parks as they drive, turning the trip into an exciting adventure. The Northway leads to various charming towns and attractions, making it easier to plan stops.
Whether you take a leisurely drive or make a day of exploring, the Adirondack Northway offers a fabulous experience. It’s not just a drive; it’s a journey through some of New York’s most beautiful scenery.
Address: Adirondack Northway, NY 12817.
11. Explore the Nearby Gore Mountain for Skiing and Snowboarding
Gore Mountain is a premier winter sports destination for skiing and snowboarding enthusiasts. Located just a short drive from Chestertown, it offers a variety of trails suitable for all experience levels. Whether you’re a beginner or an expert skier, there’s something for everyone at Gore.
With over 100 trails and numerous snow parks, visitors can spend the whole day enjoying their favorite winter sports. Ski lifts are efficient, getting you back to the top quickly, so you can maximize your time on the slopes.
In addition to skiing, Gore Mountain offers lessons, gear rentals, and friendly staff to ensure a fantastic experience. Whether you’re learning or simply enjoying the snow, the atmosphere is welcoming and energetic.
Amazing views of the surrounding mountains await you as you rip down the snowy trails. After a day on the slopes, cozy up at the lodge with a warm drink and share your adventures with fellow snow enthusiasts.
Gore Mountain truly delivers an exhilarating winter experience, making it a must-visit destination for anyone who loves snow sports!
Address: 793 Peaceful Valley Rd, North Creek, NY 12853.
12. Enjoy a Family-Friendly Day at the Chestertown Village Beach
The Chestertown Village Beach is an excellent place for a fun family outing. With sandy shores and calm waters, it’s ideal for swimming, sunbathing, and beach games. The beach offers ample space for kids to play while parents relax under the sun.
The shallow areas are perfect for younger children, making it a safe spot for family-friendly fun. Families can bring picnic baskets to enjoy meals while watching their kids splash around in the water.
A local playground nearby provides additional entertainment options for kids. Families can create beautiful memories while soaking up the summer sun.
Many visitors love to rent paddleboards or pedal boats to explore the lake from a different perspective. This adds excitement to the day and allows everyone to connect with nature.
The Chestertown Village Beach offers a delightful atmosphere where families can bond and enjoy quality time together. Don’t miss out on this great summer getaway!
Address: 94 Village Beach Rd, Chestertown, NY 12817.
13. Participate in Local Events During the Chestertown Winter Carnival
The Chestertown Winter Carnival is a fun-filled celebration that brings the community together. Each year, this event features exciting activities for all ages. From ice skating to sledding, there’s never a dull moment!
Families can enjoy various winter sports competitions and games that engage everyone. You might even witness a snow sculpture contest, showcasing the artistic talents within the community. The atmosphere is lively, with laughter and joy filling the air.
Vendors set up booths with hot food, drinks, and local crafts, providing the perfect chance to warm up and shop. The delicious food is often a highlight, with warm treats and hearty meals to refuel after outdoor fun.
Live music and entertainment keep the vibe exciting throughout the day. Families can gather around a bonfire to enjoy music or storytelling, creating wonderful memories together.
Participating in the Chestertown Winter Carnival is a fantastic way to embrace winter and connect with the community. It’s a must-see event for locals and visitors alike!
Address: Chestertown, NY 12817.
14. Experience Snowshoeing or Cross-Country Skiing on Area Trails
Exploring the snowy landscapes through snowshoeing or cross-country skiing is a delightful way to enjoy winter. Local trails around Chestertown offer a variety of scenic routes for all skill levels. These activities allow you to connect with nature in a serene, winter wonderland.
Many trails are well-marked and provide stunning views of the surrounding mountains and forests. You can feel the crisp air and embrace the beauty of untouched snow as you journey through the quiet wilderness.
Local equipment rentals are available for those who don’t have gear. Friendly staff can assist new participants with techniques and tips to keep everyone safe and comfortable.
Snowshoeing and cross-country skiing make for great family activities. It’s a perfect chance to bond while enjoying personal time outdoors. Keep an eye out for wildlife tracks as you travel through the pristine snow.
There’s nothing quite like experiencing the quiet beauty of winter on foot. Snowshoeing and cross-country skiing offer memorable adventures in the Chestertown area.
Address: Chestertown, NY 12817.
15. Check Out the Local Eateries, Like The Silver Star Restaurant
The Silver Star Restaurant is a popular local eatery that promises delicious meals in a cozy atmosphere. Known for its friendly service and inviting decor, this restaurant is a must-visit when in Chestertown.
The menu features a variety of items, including fresh, seasonal dishes that showcase local ingredients. Whether you’re in the mood for classic comfort food or something more adventurous, there’s something for everyone.
Patrons speak highly of their hearty breakfasts and mouth-watering dinners, making it ideal for any time of the day. The relaxed ambiance makes it a wonderful place to gather with family and friends.
Don’t forget to save room for desserts! The restaurant’s sweet treats are the perfect way to end your meal on a high note. Taste the sweetness of homemade pies or rich cakes that highlight local flavors.
When looking for a delightful dining experience, The Silver Star Restaurant is the place to be. Each visit will leave you with satisfied taste buds and happy memories.
Address: 6316 NY-9, Chestertown, NY 12817.
16. Go Birdwatching at the Nearby Natural Stone Bridge and Caves Park
Birdwatching at the Natural Stone Bridge and Caves Park is a rewarding experience for nature enthusiasts. This beautiful area provides unique habitats that attract various bird species. It’s a haven for birdwatchers wanting to see both common and rare species.
The park features walking trails that meander through beautiful scenery, offering the perfect vantage points for observing birds. Early morning or late afternoon is the best time for sightings, as birds are often more active then.
Several informational signs around the park educate visitors about local flora and fauna, enhancing the birdwatching experience. Bring binoculars for a closer look at the amazing birds you might encounter.
Additionally, the natural formations and caves create an awe-inspiring backdrop, making the experience even more enjoyable. It’s an excellent family activity where everyone can appreciate nature together.
Paying a visit to Natural Stone Bridge and Caves Park is an exciting way to mingle with nature and enjoy peaceful moments. Birdwatching here will surely enhance your appreciation for the natural world.
Address: 535 Stone Bridge Rd, Pottersville, NY 12860.
17. Visit the Nearby Thurman Homestead Park for Hiking and Nature Walks
Thurman Homestead Park is an ideal location for hiking and nature walks. This charming park offers picturesque trails that wind through lush greenery, perfect for outdoor enthusiasts and families alike. The trails vary in difficulty, accommodating hikers of all levels.
Many trails feature interior woods, meadows, and stunning views of the surrounding landscapes. As you hike, you might encounter various wildlife, including birds and small mammals, enhancing your adventure.
Thurman Homestead Park also has picnic areas, making it an excellent choice for a family outing. Pack a lunch to enjoy after your hike while taking in the natural beauty of the park.
Visitors often enjoy photographing the stunning views, whether it’s lush vegetation in the summer or vibrant foliage in the fall. The beauty of this park is undeniably captivating.
A visit to Thurman Homestead Park offers a perfect blend of outdoor activity and relaxation. It’s a wonderful spot to reconnect with nature!
Address: 447 County Rd 16, Thurman, NY 12885.
18. Attend Chestertown’s Annual Fair and Parade for Community Fun
The annual Chestertown Fair and Parade is a beloved tradition that draws visitors from around the area. This exciting event celebrates community spirit with fun activities, delicious food, and vibrant entertainment. It’s an ideal family outing!
The parade features local floats, bands, and community groups that bring joy and excitement to the streets. Families can gather along the route to enjoy the colorful displays and lively atmosphere.
Additionally, various fair activities are available, such as games, contests, and booths showcasing local crafts. There’s something for everyone, making it a joyous occasion for all ages.
Food vendors offer tasty treats, allowing visitors to taste local specialties while enjoying the festivities. It’s a great chance to unwind, mingle with neighbors, and make memories.
Attending the Chestertown Fair and Parade is a fun way to experience the town’s vibrant community. Participate in the celebration and embrace the joyful spirit of Chestertown!
Address: Chestertown, NY 12817.
19. Explore the Scenic Shoreline of Lake Luzerne
Lake Luzerne is a beautiful destination that’s perfect for exploring its scenic shoreline. Walking along the lake’s edge offers breathtaking views that change with the seasons. Both locals and visitors appreciate the tranquil beauty and abundant recreational opportunities.
You can access various activities, such as kayaking, swimming, or fishing, all while soaking in the stunning views. The peaceful environment allows for relaxation and reflection, making it a great escape from daily life.
The surrounding nature trails provide perfect walking paths where you can appreciate the local flora and fauna. Birdwatching along the shoreline can add an exciting element for nature lovers.
There are plenty of picnic spots along the shoreline, where you can enjoy a meal while gazing at the water. Sunset views from the shore are particularly breathtaking, painting the sky with vibrant colors.
Exploring Lake Luzerne allows for a refreshing day immersed in nature. Whether you’re looking for adventure or a quiet retreat, the shoreline is an ideal getaway.
Address: Lake Luzerne, NY 12846.
20. Try Your Luck at Local Hunting in the Extensive State Forest Lands
The state forest lands near Chestertown offer fantastic hunting opportunities for outdoor enthusiasts. With abundant wildlife, hunters can try their luck while enjoying the beautiful landscapes here. It’s a great way to connect with nature and embrace the hunting tradition.
Hunting seasons vary, and local regulations ensure responsible and ethical practices. Be sure to obtain any necessary permits and respect wildlife conservation guidelines for a successful outing.
Extensive trails and wide-open spaces provide an exciting setting for hunting enthusiasts. While pursuing game, adventurers can immerse themselves in the ever-changing environment around them.
Before heading out, connecting with local organizations or hunting groups is helpful for tips and updates on current hunting conditions. Sharing stories and experiences can enhance your adventures.
Hunting in the area is not only about the thrill; it’s also an opportunity to immerse yourself in the beauty of nature. It’s a rewarding way to spend time outdoors near Chestertown.
Address: Chestertown, NY 12817.
Final Thoughts
Chestertown, New York, offers a diverse array of activities for everyone. From outdoor adventures and art festivals to community celebrations, there’s no shortage of things to do. It’s a fantastic destination for families seeking fun and memorable experiences. If you’re interested in exploring more locations, check out the things to do in Hudson, NY or see what Pulaski has to offer with the things to do in Pulaski, NY. Whether you’re exploring the natural beauty of nearby parks, enjoying local cuisine, or engaging with the community, Chestertown has something special waiting for you. Discovering the charm of this small town will leave you with lasting memories and a desire to return.