7 Reasons Why You Should Include Chestertown In Your Adirondack Vacation Plans

Nestled in the Southeastern Adirondacks, Chestertown is a small hamlet within the Town of Chester. While the community is surrounded by other popular Adirondack destinations, such as North Creek and Lake George, Chestertown itself is a must-visit place for visitors and vacationers. Featuring great hiking spots, things to do, and more, here are 7 reasons why Chestertown should be a part of your Adirondack vacation!

Take on the Chester Challenge

palmer pond

Designed by the Town of Chester, the Chester Challenge is a hiking challenge for families and hikers of all skill levels. Centered around Chestertown, NY, the challenge is a great introduction to some of the region’s lesser known hiking and nature trails.

To complete the Chester Challenge and receive a commemorative pin, all you have to do is hike 6 out of 11 designated trails. Whether you choose to hike the easier trails, the harder trails, or a mix of both, you’re sure to feel a sense of accomplishment once you’re rewarded for completing the Chester Challenge.

Visit Two Beautiful Lakes

friends lake sunset

Friends Lake

Make Chestertown your vacation destination and book a rental or stay along the Friends Lake shoreline. Friends Lake is a private body of water, so to access it, you have to stay at local lodging property on the lake. Many of these sites are located just steps away from the water and feature private beaches and docks for you to enjoy. Just some of the possible options include Friends Lake Inn and Fern Lodge, which are perfect for a comfortable Adirondack getaway.

Loon Lake

If you’re visiting Chestertown during the summer for a day trip, there’s no better way to cool off quickly than by swimming in Loon Lake. The public beach is located on Route 9 across from The Lakeside at Loon Lake. Want to head out on the water instead? Just a few feet down the road from the beach is a public boat launch and wash station.

Shop Around

farmers market tent

Chestertown Farmers’ Market

Open from late spring to early fall, the Chestertown Farmers’ Market is the region’s premier place for fresh produce. The market’s fruits and vegetables are grown locally and picked when ripe. From trying new food to asking the vendors for advice and recipes, there is so much to enjoy during your trip there. Support the area’s farming community and shop at the Chestertown Farmers’ Market!

The Crossroads

blt sandwich

The Crossroads is a country store and outdoors shop that offers all you need and more to go on your own Adirondack adventure. Although the store specializes in fishing gear and clothing, they also sell sandwiches and soup at their deli and ice cream during the warmer months. Stop by this local hangout spot and see everything they have to offer.

Go For A Horseback Ride

three horseback riders

Located in Chestertown, NY, Circle B Ranch is a family-owned horseback riding ranch that has been making dreams come true since 1961. Set on over 500 acres of trails, forests, and wide fields, the ranch lets you experience the Adirondacks by horseback or horse-drawn ride.

Both kids and adults can take part in the fun of horseback riding at Circle B. Rides can be customized and range from pony rides for kids to group rides, private rides, and more. The ranch hands will match your skill, personality, and size with just the right horse, ensuring you have a memorable time during your ride.

Ride Along Snowy Trails

snowmobile riders

There’s nothing more thrilling during winter than riding a snowmobile through the snowy woods in the Adirondacks. Experience the excitement and adventure for yourself with C+C Adirondack Snowmobile Tours in Chestertown, NY.

Offering a combined 40+ years of snowmobiling experience, the staff at C+C will help you have the time of your life on the trails. Each tour can be customized to accommodate riders of all skill levels. All you have to do is wear your winter clothes and prepare for fun!

Enjoy Trips to the Park

dynamite hill rec center

The Dynamite Hill Recreation Area is a four-season public recreation park that features over 133 acres of land for hiking and single-track mountain biking during the warmer months and downhill skiing, cross-country skiing, snowshoeing, tubing, and ice skating during the colder months. A warming hut is available near the slopes, and a seasonal pavilion is a great spot to have a picnic with family and friends.

Try Some Tasty Local Bites

chestertown the bullhouse

The Bullhouse

For Latin American cuisine in a casual yet upscale setting in the heart of Chestertown, try The Bullhouse. Their extensive menu includes a variety of tapas/starters as well as everything from steaks to seafood and more. Check out the full bar for a wide selection of craft beers and fine wines to pair with your meal.

Panther Mountain Pub

For some of the best pub grub around, take a trip to the Panther Mountain Pub. The restaurant is popularly known for its fried food, pizza menu, live entertainment, and craft beers at the bar. You can find the local pub at the Panther Mountain Inn, which is centrally located in Chestertown.

Main Street Ice Cream Parlor & Restaurant

The Main Street Ice Cream Parlor is one of the most popular sites in all of Chestertown. You can sit right at the old-fashioned counter or grab a table for your group. For delicious icy treats, great food, and more, this ice cream parlor is the place to be. Don’t forget to browse their gift shop!

Find local lodging in Chestertown and the Adirondacks »

« Back to Things to Do

Connect With Us