Dining

Smity’s Cafe- A laid-back spot perfect for breakfast or lunch. Known for its hearty classics, fresh ingredients, and welcoming vibe—grab a seat inside or enjoy the patio when the weather’s nice
The Owl- A lively and beloved local bar and grill. With great burgers, cold drinks, and a fun, casual atmosphere, it’s a great place to unwind with friends or catch a game
Marty’s Cafe- Great for breakfast or lunch. Grab a specialty coffee, wrap, or pastry on the go or sit and relax by the windows.
Community Table- Known for its food and cocktails, this restaurant brings the highest quality, locally grown, and procured ingredients to serve its community in a chic, vibrant atmosphere
GW Tavern- Dating from 1850, this tavern serves American comfort food in cozy surrounds with a patio & hearth

Activities

Guy Wolff Pottery– A unique opportunity to experience handcrafted, functional art in a charming, rustic setting, where you can meet the artisan behind the iconic pottery
Gilmore Girls Tour- Explore the real-life charm that inspired the beloved show with a self-guided tour of the area. Start your day at Marty’s Café for a Luke’s Diner-style coffee, then stroll through New Preston Village for boutique shopping at Plain Goods and Pinnacle—perfect stand-ins for Doose’s Market or Miss Patty’s studio. Wander past The Owl for small-town bar vibes, and take in the classic New England architecture, town green, and hidden bookshops along the way
The White Gallery– For art lovers, this gallery in Kent offers a variety of contemporary works from local and national artists
Litchfield Distillery– Enjoy a tasting at this craft distillery located in Litchfield, offering spirits distilled from locally grown grains
White Silo Farm & Winery– Set in a gorgeous countryside location, enjoy wine tasting and stunning views
Kent Falls Brewing– A small, family-owned brewery in Kent, known for its great atmosphere and selection of craft beers
The Litchfield History Museum– Learn about the county’s rich history, from colonial times to the present, in a charming, rustic setting, where you can meet the artisan behind the iconic pottery

Shopping

Litchfield– A picturesque town with antique shops, art galleries, and cozy cafes. Stop by Arethusa Farm Dairy for some of the best ice cream in the area, Thorncrest Farm to try some amazing chocolate, and Bantam Bread for a tasty pastry
Kent– Known for its boutique shops and art galleries, Kent is also home to excellent dining spots like The Egg’s Nest for a delicious breakfast or brunch
Washington Depot– A quaint village with boutique shopping and cafes. Don’t miss The Pantry for locally sourced goods and great lunch options
Pinnacle- A beautifully curated boutique offering a thoughtful mix of contemporary fashion, accessories, and unique home goods. Perfect for finding a special piece or stylish gift
Plain Goods- A refined general store blending timeless style with everyday utility. Browse quality clothing, homewares, and vintage-inspired finds in an airy, minimalist space
The Treasures of the Litchfield Hills– A hidden gem, this collection of antique shops offers everything from fine furniture to unique collectibles
The Antiques Center of Litchfield– A multi-dealer antique store offering a wide selection of vintage and unique items

Nature/Hikes

Kent Falls State Park– A must-visit for nature lovers. Hike up the trail to the top of the beautiful Kent Falls, a waterfall that drops over 250 feet
Bantam Lake– The largest natural lake in Connecticut, perfect for a leisurely walk along its shores or a peaceful boat ride
Mount Tom State Park– A great spot for panoramic views of the surrounding hills, with trails for all levels of hikers
Hollenbeck’s Pond– This historic spot offers not only scenic views but a peaceful location for relaxation or a quiet picnic