A Winter Day Trip from Litchfield County: Hikes, Small Town Stops, and a Sunset

Amber in New England
6 days ago
4 min read

Updated: 22 hours ago

Amber in New England | January 2026

Winter in the Hudson Valley and Northwest Connecticut is quiet and full of adventure if you know where to go. On January 2, we mapped out a day trip that hits small towns, waterfalls, fire towers, and a peaceful sunset by a hidden pond, all within about three hours of driving.

This is the perfect mix of hiking, coffee, views, and a little post-adventure indulgence. Here’s how your day an go.

🗺️ Map of the Route

⏰ Quick Day Trip Timeline

Stop	Drive Time from Previous	Notes
Litchfield County → Bagel Co, Great Barrington, MA	46 min	Start your morning right with coffee & bagels. Parking can be tricky.
Bagel Co → Fuel, Great Barrington	2 min	Grab a second round of drinks if needed; lots of options.
Fuel → High Falls Conservation Area, NY	33 min	First hike of the day, be ready for icy conditions.
High Falls → Stissing Mountain Trail, NY	34 min	Moderate hike with fire tower views.
Stissing Mountain → Rudd Pond, NY	22 min	Walk to gazebo for sunset; icy edges, stay back.
Rudd Pond → Oakhurst Diner & Oblong Books, NY	7 min	Soups, sandwiches, and a charming bookstore stop.
Millerton → Litchfield County	40 min	Return home after a full, scenic day.

☀️ Morning Start: Bagels & Coffee in Great Barrington, MA

We started off at Bagel Co on Main Street. If you’re a bagel enthusiast, this place is heaven! Over a dozen bagel flavors, creative cream cheeses (red onion and chive), and great sandwiches. It never disappoints.

Inside of Great Barrington Bagel, showing the menu on the wall.

Next, just a short 2-minute drive away is Fuel, perfect for grabbing a round of coffee or tea. They have vegan options available (oat milk and almond). They have plenty of drink options, but parking is limited on Main Street, so plan ahead.

Inside of Fuel in Great Barrington, MA for coffee and tea. Showing the pastries by the register.

❄️ Winter Hiking: High Falls Conservation Area

From Great Barrington, it’s about 33 minutes to High Falls Conservation Area in New York. We took the Green and Blue Trail (AllTrails link here), an easy 1.5-mile loop with a few icy stretches, so pack crampons/spikes.

The waterfall itself is dramatic in winter. Ice sheets cling to the rocks, possibly making it even more striking than in summer. Traction is mandatory here, and I HIGHLY recommend microspikes or crampons (see my full winter hiking tips) if you’re attempting the loop.

The route is straightforward, hiking up to the platform then to the base of the waterfall, crossing a small stream, and returning to the parking lot. There are other short trail options here if you want to extend your hike, but this route gives a quick payoff and fits perfectly into a day trip.

🏔️ Midday Adventure: Stissing Mountain Fire Tower

Next, we drove 34 minutes to Stissing Mountain. We took the Stissing Mountain Trail (AllTrails link here), a steep 1.9-mile out-and-back hike.

The climb is steady, with about 900 feet of elevation gain in less than .8 miles. At the summit, the fire tower offers 360-degree views of the Hudson Valley and surrounding peaks. Even in winter, the visibility is amazing. Minimal crowds make this a standout stop.

Other trails exist around Stissing Mountain, but this trail gives the best combination of distance, challenge, and views for a single winter day.

This is a great place to do a sunrise hike! Bookmark this for an early morning wake up

🌅 Sunset Stop: Rudd Pond, NY

After descending, we drove 22 minutes to Rudd Pond. We parked and walked to the gazebo to watch sunset. It was icy along the pond’s edge, so be careful. Do not step out onto the frozen surface. If you’re a photographer or just want to soak in quiet, this is a perfect mid-to-late afternoon stop.

🥣 Post-Hike Eats & Bookstore Browsing: Millerton, NY

A short 7-minute drive brings you to Oakhurst Diner for delicious soups and sandwiches. After that, we wandered into Oblong Books, a cute independent bookstore with unique gift items.

This combination of food, caffeine, and browsing rounds out the day perfectly.

🔄 Return to Litchfield County

Finally, it’s about 40 minutes back home to Litchfield County, leaving you with plenty of memories, photos, and maybe a few extra bagels to enjoy later.

✅ Quick Tips for This Day Trip

Weather & Traction: Winter conditions make High Falls and Stissing Mountain icy. Bring traction and layer appropriately (see my winter layering guide).
Parking: Main Street in Great Barrington can be tight. Arrive early or plan for a quick walk.
Timing: Aim to leave Litchfield County by 9-9:30 AM to fit everything comfortably.
Food: Great Barrington Bagels for breakfast, Fuel coffee to go, and Oakhurst Diner for post-hike comfort. Don’t skip Oblong Books.