Hey neighbor!
If you’ve ever stood at the counter of the Berkshire Country Store, you know how much we love chatting the local region. Whether you’re visiting from say nearby Winsted or just on a day trip for some fresh air and new views, this corner of New England is home to some of the most rewarding hiking spots around. Nestled in the heart of Northwest Connecticut, right along the edge of Southwest Massachusetts, Norfolk serves as a perfect launch point to explore trails that wind through the Litchfield Hills and into the Berkshires.
So grab your hiking boots and maybe one of the best breakfast sandwiches around for the road—here are five incredible hikes in the Litchfield Hills and Berkshires, each with their own charm, natural beauty, and a little local flavor.
Haystack Mountain State Park – Norfolk, CT
A favorite with locals (ourselves included), Haystack Mountain is a quick hit of big views without a long haul. The highlight? A 34-foot stone tower, built in 1929, perched atop a 1,716-foot peak that looks out across four states—Connecticut, Massachusetts, New York, and Vermont. If that doesn’t take your breath away, the trail will.
There are two ways up:
A paved road for a more leisurely stroll
Or a more rugged trail loop that climbs through the woods
No matter which you choose, the payoff is a panoramic view of the entire region—especially beautiful in the fall or when the mountain laurel blooms in early summer.
Directions to Berkshire Country Store from Haystack Mountain
Trail Snapshot: Haystack Mountain Trail
| Feature | Detail |
|---|---|
| Trail Name | Tower Loop Trail & Road Trail |
| Length | ~1 mile (trail loop), 2 miles (road) |
| Elevation Gain | Moderate |
| Difficulty | Easy to Moderate |
| Special Features | Historic tower, panoramic views of 4 states |
| Parking | Seasonal availability near summit |
| Fees | Free for CT residents; fees may apply for others |
| Recent Conditions | Generally well-maintained |
Kent Falls State Park – Kent, CT
Get the Kent Falls Trail Map Here | Directions to Kent Falls State Park
Just a short drive from Norfolk, Kent Falls is where the sound of cascading water guides your journey. Known for its spectacular series of waterfalls, this park is a family favorite and great for photographers.
You’ll find:
An ADA-accessible path to view the lower falls
A stone stair trail that runs beside the cascade with multiple scenic platforms
Shaded picnic areas for a post-hike snack (maybe pack one from us!)
Directions to Berkshire Country Store from Kent Falls
Trail Snapshot: Kent Falls Steps Trail
| Feature | Detail |
|---|---|
| Trail Name | Kent Falls Steps Trail |
| Length | 0.84 miles (out-and-back) |
| Elevation Gain | Moderate |
| Difficulty | Moderate |
| Special Features | Waterfalls, picnic areas, ADA access at base |
| Parking | On-site lot |
| Fees | State park access applies |
| Recent Conditions | Accessible year-round, some trail elevation |
Sandy Brook Trail – Colebrook, CT
Get the Sandy Brook Trail Map Here | Directions to Sandy Brook Trail
Tucked away in a stretch of protected land in Colebrook, Sandy Brook Trail is a quieter alternative perfect for those craving solitude. You’ll walk along peaceful streams, through mixed hardwood forest, and past signs of rich biodiversity that make this loop a hidden gem of Northwest CT hiking.
This trail is a new addition to the area. Part of a larger conserved area that includes Algonquin State Forest and Aton Forest, and it’s a great place for wildlife spotting and birdwatching.
Directions to Berkshire Country Store from the Sandy Brook Trail
Trail Snapshot: Sandy Brook Trail
| Feature | Detail |
|---|---|
| Trail Name | Sandy Brook Trail |
| Length | 1.5-mile loop |
| Elevation Gain | ~100 ft |
| Difficulty | Moderate |
| Special Features | Mountain stream, quiet forest, wildlife habitat |
| Parking | Roadside grassy area |
| Fees | None |
| Recent Conditions | Clean, moderate incline, easy to navigate |
Monument Mountain – Great Barrington, MA
Get the Monument Mountain Trail Map Here | Directions to Kent Falls State Park
Just across the border in the Berkshires, this stunning hike blends natural beauty with literary history. Writers like Nathaniel Hawthorne and Herman Melville once climbed these trails—and it’s easy to see why. Monument Mountain’s summit offers views of Southern Berkshire County and the Housatonic River Valley that are worth every step.
There are three main trail options to create a loop hike:
The Mohican Monument Trail for moderate access
The Hickey Trail if you’re looking for a challenge
Or Peeskawso Peak for direct views and the summit
Picnic tables near the parking area make it a perfect spot to relax post-hike.
Directions to Berkshire Country Store from Monument Mountain
Trail Snapshot: Monument Mountain Loop
| Feature | Detail |
|---|---|
| Trail Name | Mohican Monument, Hickey, Peeskawso Peak Trails |
| Length | 3–3.5 miles |
| Elevation Gain | 700–1167 ft |
| Difficulty | Moderate to Strenuous |
| Special Features | Literary history, panoramic views, Devil’s Pulpit |
| Parking | $6 fee for non-members |
| Fees | Free for Trustees of Reservations members |
| Recent Conditions | Rocky and steep in parts, especially early spring |
Race Brook Falls – Sheffield, MA
Get the Race Brook Falls Trail Map Here | Directions to Race Brook Falls Trailhead
If you’re up for a longer, more adventurous outing, Race Brook Falls offers a dramatic reward. This trail leads to a series of waterfalls, and for more seasoned hikers, continues on to the summit of Mount Race, part of the Appalachian Trail corridor.
It’s a 5.7-mile round trip if you go all the way to the top, with a 3-mile loop to the falls if you’re short on time. Either way, the lush woods and cascading streams make this a standout trail in Southwest Massachusetts.
Directions to Berkshire Country Store from Race Brook Falls
Trail Snapshot: Race Brook Falls Trail
| Feature | Detail |
|---|---|
| Trail Name | Race Brook Falls to Mount Race |
| Length | 3 miles (falls only), 5.7 miles (summit loop) |
| Elevation Gain | Moderate to High |
| Difficulty | Moderate to Strenuous |
| Special Features | Waterfalls, summit views, connects to Appalachian Trail |
| Parking | Small lot at trailhead |
| Fees | None |
| Recent Conditions | Trail conditions may vary seasonally |
Tips for a Great Hike in Northwest CT & the Berkshires
Bring water (and maybe a snack from the store!)
Dress in layers—spring can be tricky
Check the weather before heading out
Wear good boots—many of these trails have uneven terrain
Let someone know your plans, especially if heading out solo
And of course, Leave No Trace
Fuel Up at the Berkshire Country Store in Norfolk, CT
Before you hit the trail—or after you’ve clocked those miles—swing by and say hello. We’ve got just what you need:
Hot coffee and breakfast sandwiches in the morning
Fresh deli sandwiches and salads for lunch or takeout
Baked goods and snacks for the trail
And maybe just a neighborly conversation about your favorite view from the top
Get directions to the store – Located in the heart of Norfolk, CT
(Click to Enlarge)
Conclusion: Your Next Great Hike Starts Here
From tower-top views and forested streams in Northwest Connecticut to literary legends and waterfall treks in the Berkshires, these five trails offer something special for every hiker—whether you’re a casual weekend walker or a seasoned summit-seeker.
And no matter where your boots take you, we’ll be here in Norfolk at the Berkshire Country Store, ready with hot coffee, fresh sandwiches, sweet treats, and a warm welcome to keep your day fueled.
👉 Explore our full menu here to see what’s cooking before or after your hike.
👉 Browse the Berkshire Country Store Area Guide for more local adventures, food spots, and hidden gems across Northwest CT and Southwest MA.
Adventure starts here—and we’re always glad to be part of yours.
Hiking Near Norfolk, CT and the Berkshires — Frequently Asked Questions
You’re in luck—Norfolk is surrounded by some truly special trails. We always recommend starting with Haystack Mountain State Park for its short but rewarding climb and panoramic views.
Monument Mountain is steeped in literary history—Nathaniel Hawthorne and Herman Melville hiked it together in the 1800s, and it’s said to have helped inspire Moby Dick. You’ll find markers and stories woven throughout the trail.
Late spring through fall is ideal—May to November offers wildflowers, summer greenery, and stunning foliage. But if you’re winter-ready, snowshoeing or microspike hiking in the colder months is peaceful and beautiful too.
Absolutely. Kent Falls, it’s not too long or steep, and each has something special to see.
Visit official park websites like The Trustees of Reservations or state park pages. Apps like AllTrails and Hiking Project often have up-to-date reviews. Or swing by the store—we’re always happy to share what we’ve heard from hikers that day.
Yes, but be prepared. Most trails are open year-round, but access roads may be closed and conditions can get icy. Bring traction gear like microspikes and warm layers, and always check weather conditions ahead of time.
We recommend layered clothing, waterproof boots, bug spray, sun protection, and plenty of water. Trails can be muddy or cool in the mornings. And of course, pack snacks—or stop by the store for trail mix and a sandwich to-go!
You’re already there—The Berkshire Country Store in Norfolk is a perfect stop. We’ve got hearty breakfast sandwiches, fresh deli lunches, pastries, coffee, and cold drinks. Fuel up before you hit the trail, or swing by after for a treat and a chat!
