*To learn more about the Chester Challenge, check out our Chester Challenge Page.
Lunch – Main Street Ice Cream Parlor
Once you’ve finished your treks, venture on over to the center of Chestertown for lunch at Main Street Ice Cream Parlor.
If you’re a fan of classic vibes and nostalgia, then you’ll love this old-fashioned parlor, which was originally built as a schoolhouse. This restaurant serves homemade soups and salads, signature burgers, and, of course, ice cream—including authentic sodas, floats, and even malted milkshakes.
And, once you’re done with your meal, spend some time checking out the designer boutique and gift shop upstairs for some original Adirondack souvenirs.
Pictured: Inside Main Street Ice Cream Parlor
Afternoon – Hit the Beach
Enjoy a fun afternoon at the beach by going to the Loon Lake Public Beach. This small sand beach has a swimming area, with both shallow and deep areas well marked.
Besides swimming, though, you can also cast your fishing line on the water, or use the nearby small hand boat launch to take your canoe or kayak out on the lake.
Loon Lake also has some spectacular views of the Adirondack mountain ranges in the distance, creating some excellent photo opportunities if you are equipped with your phone or camera.
Pictured: Loon Lake Public Beach; Photo Credit: Kacey O'Brien
Afternoon/Evening – Horseback Riding
Navigate through the serene Adirondack Forest on horseback with a guided scenic trail ride at Circle B Ranch. This family-owned ranch has been offering tours for all levels of riders for over 50 years.
You can choose from the 1-Hour Beaver Dam Trail Ride, where you’ll be able to spot local nature and wildlife. Journey through Adirondack forest and marshland as your guide narrates fun facts along the way.
Or if you’d like to wait a little bit later, you can experience their newer Sunset Mountain Ride, and watch the sun begin to set from the top of a mountain lookout.
No matter which option you choose, this makes for a fun and unique opportunity to partake in.
Trail Times
- Beaver Dam Trail Ride – 1:30 PM or 3:00 PM
- Sunset Mountain Ride – 6:30 PM (*Only on select days!)
To learn more or to book, check out our Circle B Ranch listing.
Dinner – The Remington on Main
Savor true American fare at The Remington on Main—located on Chestertown's Main Street.
Step inside to marvel at the cozy décor, be welcomed by a friendly atmosphere, and prepare your taste buds for mouthwatering entrees, including pastas, salads, and other specialties. You can even pair your meal with a fine glass of wine to cap off an eventful day.
Day 2 – Brant Lake/Pottersville
The second day will have you exploring the other communities within North Warren. Brant Lake, Pottersville, and even the small hamlet of Adirondack. These areas are surrounded by the beauty and serenity that is the Adirondack Park, making them fantastic destinations for outdoor adventure.
Morning – Cave Exploring
Adventure through the largest marble cave entrance in the Eastern U.S. at Natural Stone Bridge and Caves with their self-guided cave tour.
Witness incredible displays of ancient Adirondack geology on this above-ground trail that features the massive Stone Bridge, Trout Brook, and an assortment of naturally formed potholes and grottos.
This 20-stop trek takes an average of 45 minutes to an hour, but there are also other activities to check out at Natural Stone Bridge and Caves, including:
- An 18-hole disc golf course
- Access to the Green Hill and Catamount Mountain hiking trails
- Rock & Mineral and Gift Shops for some fun mementos
*Please Note: Tickets are recommended being purchased in advance to ensure availability.
Pictured: Exploring Natural Stone Bridge and Caves
Lunch – The Hub
Gear up for the afternoon at Brant Lake’s popular hangout, The Hub.
Their inside bar and café serves delicious homemade bites. From specialty sandwiches and salads to personal pizzas.
But The Hub is more than a simple eatery; they are the activity center for biking, hiking, or paddling around the Brant Lake area. Not only can you get your bike repaired at their in-house service shop, but also their staff are terrific resources for outdoor recreation planning and guidance.
Afternoon – Choose Your Own Adventure(s)
After your pit stop, you actually have multiple choices for how to spend your afternoon.
Mountain Biking
The Brant Lake Bike Park is a professionally built single-track trail system spanning over five miles of terrain. Plus, there’s a majestic unobstructed view of the lake.
Setting Sail on the Water
Embark for a lovely afternoon on Brant Lake with Brant Lake Marina. From there, you can acquire from a selection of rentals available for use.
- Pontoon Boats
- Canoes
- Kayaks
- Fishing Boats
Swimming
For a more relaxing activity, you can go for a swim at the Brant Lake Beach. This beach has a medium-sized swimming area right on Mill Pond, plus there’s also a floating dock for lounging.
Dinner – Café Adirondack
Savor a perfect dinner to conclude the past two days by heading to Café Adirondack, located in Pottersville.
This humble little abode is actually a full-scale restaurant and wine room, serving various pastas, seafood, sandwiches, and more. Meanwhile, you can also sample a premium list of white, red, and sparkling wines, not to mention some local IPAs.
Lodging Options
Need someplace to stay while you’re completing this itinerary? Check out some recommended local accommodations.
