A Summer Getaway: 48 Hours in Washington, CT

With breathtaking natural beauty, world-class culture, and a charming small-town feel, Washington is the perfect destination for your summer getaway. This picturesque New England town nestled in the rolling hills of Litchfield County, Connecticut offers countless ways to unplug, unwind, and be inspired by the lush beauty of the summer season.

Washington’s abundant arts and cultural events, beautiful vistas and hiking trails, and extraordinary shopping and dining around town offer something for everyone to enjoy. Let your summer getaway begin! And download our Guide to Washington for a list of all things to do, shopping, and dining in town.

DAY 1: Exploring Washington Depot

As you arrive, get your first taste of Washington in the heart of town, called “The Depot” by locals, where you can explore casual eateries, chic shops, and art galleries. There you’ll find the Welcome Center, located at 6 Bryan Hall Plaza, where you can pick up maps and guides, find public restrooms, and view a pop-up historical exhibit created in partnership with the Gunn Historical Museum. Stop by to check it out!

From there, head over to Marty’s Cafe where you’ll find breakfast, lunch, and bakery items prepared with fresh locally-sourced ingredients and outdoor seating – the perfect perch for people-watching. Another foodie favorite is The Pantry, where you can grab a coffee and an ever-changing menu of delectable breakfast items, pastries, salads, and sandwiches.

Next, stroll over to Judy Black Memorial Park and Gardens to enjoy their lush summer blooms and sculpture garden and find inspiration with their latest art exhibit on display. If you’re in town on a Saturday, you can also see what goodies you can find at the Washington Farmers Market from 9:30am to 12:30pm, accompanied by live music.

Make sure to pop into the charming shops in the Depot to see what items catch your fancy. You’ll find chic clothing and accessories at Five Janes, as well as merch for Gilmore Girls fans. For the latest best-sellers, unique novels, and games for all ages, browse the Hickory Stick Bookshop, a beloved independent bookseller that is a destination in itself. Visit George Home for a curated collection of mid-century modern, vintage, and antique home decor with global inspiration. And you can even find the perfect gift for your fur babies at Depot Dog!

And while you’re in the Depot, be sure to spend some time at the Washington Art Association & Gallery to view the latest exhibit or participate in an art workshop. WAA is celebrating its 70th year as a hub for visual arts in the Litchfield Hills. Also, visit KMR Arts to view the latest art on display and peruse the Hen’s Nest Gallery for eclectic finds.

Gardens, Wine Tastings & Views

A wonderful way to spend a sunny summer afternoon is a stroll through Hollister House Garden, one of Washington’s “can’t miss” gems. This classic English garden, situated in the rolling hills of Litchfield County, attracts visitors with its beautiful landscapes, a diverse palette of stunning plantings, and special events and workshops for avid gardeners and novices alike. View Hollister House Garden events

Be sure to also visit the classical Shakespeare Garden at The Mayflower Inn & Spa and grab a bite or drink at the Tap Room for casual dining or the Garden Room for an elegant dining experience overlooking the garden.

In the afternoon, plan a visit to Hopkins Vineyard up in New Preston to enjoy wine flights, cheese platters, and live music on Saturdays and Sundays in a gorgeous setting overlooking Lake Waramaug. Also visit the scenic Spring Hill Vineyards for immersive art experiences on their unique property along with wine tastings and small bites on weekends.

Outdoor Dining & Summer Evenings

After a summer day at the vineyards, it’s time for a delicious dining experience! Make your reservations at The White Horse, Community Table, or The Mayflower Inn for exciting specials, fresh ingredients, and great ambience. If you’re looking for classic dinner with a view try the beloved GW Tavern for a true New England vibe or Hopkins Inn for Austrian fare, featuring lederhosen and dirndl-clad wait staff.

In the evening, plan to watch the sunset over Lake Waramaug for a peaceful way to end the day. Or if you’re looking for more to do, check our Events Calendar for exciting summer events including Music on Main in New Preston Village, First Friday Movies at Judy Black Park, Washington Friends of Music Summer Concerts, and more.

DAY 2: Morning Hike with a View

If you’re an early riser, a morning hike is the perfect way to start your day. Washington is known for its beautiful hiking trails and natural scenery. The trails of the Steep Rock Association offer some of the best hikes and views in the area. Whether you are a beginner or an experienced hiker, you will enjoy exploring the expansive vistas and “hidden treasures” of the trails, including the Instagram-favorite Thoreau Bridge at Hidden Valley Preserve, the Railroad Tunnel at Steep Rock Preserve, or The Lookout at Macricostas Preserve on your way to panoramic views from Waramaug’s Rock.

Shopping in New Preston Village

Next, head over to explore the charming New Preston Village. Enjoy a hearty breakfast at The Smithy Cafe at 9 Main with a view overlooking New Preston Falls. Then enjoy the “small village, big shopping” in New Preston Village, a true luxury shopping destination.

Find beautifully curated home decor at Dawn Hill Antiques, Privet House, and Pergola Home. For unique fashion finds, visit J. Seitz & Co, a quaint department store that carries the latest summer styles. Plain Goods is a not-to-miss destination for timeless and thoughtfully curated clothing and accessories, also known for its award-winning renovation of a historic building anchoring the village.

For a special memento, pop into the jewel box Hays Worthington boutique where you’ll find exceptional fine and period jewelry. Next door, DK Schulman Design carries a unique collection of gift items and sophisticated stationery. And reward yourself with an amazing selection of chocolates and sweet treats from around the world at Sweeets, a sweet shoppe like no other.

Soak up the Sun at Lake Waramaug

After a morning of shopping and inspirational browsing, it’s time to beat the heat with a dip at Lake Waramaug, the second-largest natural lake in Connecticut, known for its clean waters and breathtaking scenery. This majestic lake is the perfect spot to enjoy kayaking, paddleboarding, boating, and fishing. Rentals are available at Clarke Outdoors, open seven days a week at Lake Waramaug State Park. And you’ll be sure to work up an appetite, so order a delicious picnic lunch from The Owl Wine & Food Bar or The Smithy at 9 Main and enjoy the scenery.

Historic Stroll through the Washington Green

After a day in the sun, wind down with a step back in time at the Washington Green Historic District, which encompasses the village’s green as well as much of the surrounding village center. Famous architect Ehrick Rossiter designed several buildings within this Historic District including his personal residence. Walk over to the Gunn Historical Museum to view the award-winning “Washington, Connecticut – An American Story” exhibit featuring the unique people, places, and events that have shaped Washington’s rich history. The museum hosts free guided tours every Saturday at 1:00pm.

For an afternoon pick-me-up, pop into The Po Cafe for the best view overlooking the quintessentially New England Green to enjoy swoon-worthy baked goods, inventive sandwiches, and lobster rolls. The perfect place to recap the weekend… and plan your next trip back to Washington!

Where to Stay

Make sure to plan ahead for accommodations for your time in Washington. The inns and bed & breakfasts in and around Washington offer charming New England style and hospitality for every style.

• For a luxurious experience, book a night at the Mayflower Inn & Spa and enjoy their indoor and outdoor pools, fabulous dining experiences, beautiful grounds and gardens, and spa services at THE WELL.
• For a casual inn experience, book a stay at Windemere Bed and Breakfast where you’ll find a quiet and peaceful setting with expansive views, or stay at The Hopkins Inn for gorgeous views of Lake Waramaug.
• Looking for a home rental for a larger group? PoshPadsCT offers a collection of beautifully renovated country rental homes where you can get a chance to immerse yourself in a true living experience in idyllic Litchfield County.

We hope you enjoy the perfect getaway to Washington, Connecticut this summer!

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