New York has a reputation for many things and adventure is almost always a part of the equation. Even when you think New York state couldn’t get anymore compelling for nature-lovers, another hidden spot pops up. The hidden treasures are particularly abundant in New York’s Adirondack region, whether it is a perfectly quaint town hiding in the Adirondack Mountain foothills or a top secret Adirondack hike and a waterfall that gives Nordic Fjord vibes. There is one destination that deserves a spot on your to-visit list if you’re craving a lakeside getaway: Chestertown.
Located in New York’s southern Adirondacks, Chestertown is a hamlet within the town of Chester. Even while situated near two heavy-hitting destinations for nature-lovers — North Creek and Lake George — it remains one of the best destinations to slow down and be charmed by the surrounding forests and trails. The town of Chester created its own challenge — the Chester Challenge — to encourage visitors to hike 11 of the town’s trails (with a little incentive if you manage to hike 6 of them), which is a popular activity for those visiting Chestertown.
Generally, the best time to visit Upstate New York is during summer, especially during May and August to make the most of the warmer days. However, visiting in the winter will allow you to indulge in the pristine, snow-white landscape. To get to Chestertown from New York City without a car, you’ll need to take a combination of buses which takes roughly 6 hours in total. The nearest airport to Chestertown is Albany airport. If you’re traveling by car, the journey from Albany airport to Chestertown takes just over 1 hour and 20 minutes.
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Where to find delicious food in Chestertown
Plate of chicken and rice with vegetables from The Loon restaurant – The Loon / Facebook
New York has a reputation for underrated dining scenes that leave a huge impression and, despite its small size, Chestertown is no exception. The town has a number of top-visited restaurants all with stunning views and the sounds of nature to accompany you. The restaurant The Place is located in the heart of Chestertown and known for its rustic and cozy environment. Guests particularly appreciate the “1980s Mondays” incentive, where certain menu items are priced as they would’ve been during the 1980s. The Italian American restaurant boasts a family-friendly environment and a reputation for comforting homemade meals. Some of the menu items include classic Italian dishes such as house made lasagna and meatballs and pasta, as well as house specials which include shrimp scampi over pasta and penne al vodka.
Another popular dining choice when visiting Chestertown is The Loon Restaurant and Tavern. The American-style restaurant champions locally sourced ingredients to create dishes which center local cuisine, all while offering stunning views of the Loon Lake. The restaurant even had a claim to fame when the eatery was replicated for the television series “Escape at Dannemora,” which aired in 2018. The restaurant offers a range of choices including subs, burgers, quesadillas, steaks, and salads. The specials include items such as crab cakes, veal parmesan, pink lemonade cake, and more.
Where to enjoy adventure in Chestertown
Horseback riding trail – Aimintang/Getty Images
There are several boutique hotels, lodgings, and accommodation options in and around Chestertown that are perfect for an adventure-filled stay. Friends Lake Inn is one of the most notable lodging options located on the picturesque Friends Lake and is especially popular with couples. Friends Lake Inn offers a variety of rooms, from lake-view lodging options to cabins. Another popular lodging option is The Fern Lodge which offers a private and elegant place to retreat to, while boasting a 2-mile hike for guests to explore. Expect to stay cozy with stone-walled fireplaces, lakeside fire pits, and outdoor jacuzzis. The hotel offers five luxury guest rooms, all with king-sized beds and lakeside porches to take in the views.
If you want to maximize your time on the water, renting a kayak, paddle board, or motor boat might just be the way forward. With Loon Lake Marina, a local company that has been in operation for over 50 years, you can rent from anywhere between 8 hours to 7 days. If you’d like to get in for a swim at Loon Lake, there is a sandy section where visitors can enjoy time in the marked deep or shallow ends.
If horseback riding is up there as one of your favorite activities, then Chestertown won’t disappoint. One of Chestertown’s family-friendly locations for horseback riding is Circle B Ranch. The ranch provides plenty of trails complete with mountain views to take in along the way. As a family-owned and operated ranch since 1961, the ranch has expertly been guiding visitors around the natural Chestertown landscapes for decades. The trails range from 1 to 3 hours long and are beginner-friendly.
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