Exploring the Hills & Valley
This itinerary is all about packing in the fun within a tight radius. Charming towns, local eats, and hidden gems are all nearby — so you can do more and stress less. Pick your favorites, plan your days your way, and leave room for unforgettable detours. You can even view all the spots on the map at the bottom!
Craving a getaway that blends charm, adventure, and serious relaxation? Explore Litchfield Hills and Naugatuck Valley for the perfect mix. Think rolling countryside, cozy inns, scenic trails, and small-town gems — all just a drive away. It’s the perfect escape to unplug, explore, and recharge.
- Spring
- Summer
- Winter
- Fall
- Stay Over
- Get Your Hike On
- Relax to the Max
- Savor Great Flavors
- Take the Wheel
- Go Antiquing
- Jam Out
- Visit a Museum
- Marvel at Murals
- Attend Events on the Farm
- Have a Chocolate Experience
- Hit the Slopes
- Hang by the Water
Stay Over
Start your adventure by locking down a dreamy home base. These stunning inns offer more than just a place to sleep — they bring charm, character, and a touch of magic to every moment of your stay.
Get Your Hike On
When in Litchfield Hills and Naugatuck Valley, hiking is a must. The area is home to can't-miss trails — some even boasting impressive waterfalls. Explore the suggestions below to find your perfect hike.
Relax to the Max
While you're up in Litchfield Hills, treat yourself to a spa day — because the area has the best of the best.  For the ultimate indulgent pampering experience, head to the five-star Winvian Farm in Morris — named the nation's #2 desination spa, by Condé Nast Traveler. The 5,000-square-foot spa offers facials, massage, body wraps, manicures and pedicures in one of six unique treatment rooms, including the Forty Winks Suite, featuring a wood-burning fireplace.
Visit the Mayflower Inn & Spa in Washington and discover the shimmering pool, mosaic domed whirlpool and the subtly scented Thermal Sanctuary. The Spa House offers fully equipped exercise studios including a private pilates studio and outdoor yoga and meditation garden. The salon caters to your beauty needs with manicures, pedicures and hair treatments.
Also tucked away in the scenic Litchfield Hills, The Spa at Litchfield Hills offers a peaceful escape with world-class service. From custom facials to luxe massages, whirlpool pedicures to a full-service salon, every detail is designed for relaxation. With tranquil views and a commitment to natural, client-focused care, this destination delivers the ultimate retreat for body, mind, and spirit.
Savor Great Flavors
Get a taste of The Hills and The Valley. Discover farm-to-table freshness, seasonal menus, and locally sourced ingredients — many from the region’s own rolling farms and orchards. Expect charming cafés, upscale inns, chef-driven restaurants, and homemade chocolate and cheeses. Ready to dig in? Start with the suggestions below.
Take the Wheel
If you're looking to spike your adrenaline, buckle up for a guided UTV tour with Backyard Adventure UTV Tours. You’re in the driver’s seat, tearing through hundreds of acres of private trails in a top-of-the-line UTV. With rugged terrain, stunning views, and serious thrills, this is off-roading you'll never forget.
Go Antiquing
If you’re into antiques, you already know Connecticut’s a goldmine. But here’s a hot tip: Martha Stewart herself dubbed Woodbury “The Antiques Capital of Connecticut” — and for good reason. With a treasure trove of shops packed with vintage gems, this charming town is a must-stop for collectors. Learn all about it here.
Jam Out
Music lovers won’t want to miss this stop! Built in 1883 in picturesque Norfolk, the beautifully renovated, award-winning Infinity Music Hall is an intimate music destination. Hosting more than 200 shows annually across a wide range of genres, it offers the ultimate entertainment experience. Infinity Hall is also the proud home of CPTV’s Infinity Hall LIVE — a nationally syndicated concert series unlike any other, showcasing everything from blues and folk to indie rock and zydeco.
Visit a Museum
Step into the unexpected at the area's top museums. From carousel craftsmanship to rich cultural history and amazing art, these hidden gems offer a fascinating mix of the quirky, the classic, and the thought-provoking. Explore the museum recommendations below.
Marvel at Murals
Don’t miss the bold, larger-than-life murals at the American Mural Project in Winsted — the largest indoor collaborative artwork in the world at 120 feet long and five stories high. A powerful tribute to American workers, it inspires creativity, celebrates contribution, and anchors hands-on education for all ages.
Attend Events on the Farm
While you're in the area, see what's going on at South Farms, a picture-perfect rural venue that comes alive year-round with events. From laid-back summer socials to chef-led dinners, wine tastings, live music, and comedy nights, there’s always something special happening on the farm.
Have a Chocolate Experience
Thorncrest Farm & Milk House Chocolates offers a one-of-a-kind experience: handcrafted, small-batch chocolates made with milk from cows you can meet on-site. You can even choose which cow made your chocolates!
Their “Single Cow Origin” chocolates start with pure, farm-fresh milk from pasture-raised cows fed sweet, homegrown hay. Paired with natural flavors and the world’s finest cocoa, these artisanal treats are as unique as they are delicious — a true farm-to-chocolate experience.
Hit the Slopes
Visiting in winter? Take advantage of the fantastic ski and snow sport destinations in the region.Â
As Connecticut’s original ski spot, Mohawk Mountain delivers classic winter fun with 26 trails across 107 acres, a 650-foot vertical drop, and a summit at 1,600 feet. With day and night skiing, snow tubing, on-site dining, and a full-service ski shop, it’s a top pick for snowy thrills.
Ski Sundown brings serious slope cred with 17 trails (16 lit for night skiing), two terrain parks, and a top-tier snowsports school. Open daily until 10pm with 100% snowmaking and pristine grooming, it’s a go-to for skiers and snowboarders of all levels.
Hang by the Water
Visiting in summer? The lakes and water parks in this region bring big fun. Check out some of the spots listed below.









