Choose Your Own Adirondack Adventure

Written for LakeChamplainRegion.com by the Westport-Wadhams Community Alliance (WWCA)

For Northeast urbanites yearning for a quick weekend trip where bountiful local art meets natural beauty, the little lakeside town of Westport, NY, delivers an unexpectedly robust blend of recreation and relaxation. Located on the Adirondack Coast, this historic port town and once bustling train depot for Manhattanites' summer retreats has seen a renaissance of once-shuttered businesses greeting new residents and visitors who come to revel in Westport’s range of outdoor pursuits and savor local art and agriculture at a more leisurely pace.  

Day 1: An Exploration of Art and Architecture  

Morning:  

Ease into the weekend with a freshly roasted coffee at JAMBS in the downtown historic district. From here, Walk the Westport Chair Trail, a whimsical art installation weaving through the town, featuring hand-crafted Adirondack chairs that transform public spaces into vibrant exhibits.  

Afternoon:  

Enjoy an architectural walking tour of the Heritage House district. This hub of history and culture offers a gateway to Westport's elegant 19th-century homes, built by the area’s early industrialists. Next, dine on the deck of the casual and friendly Mountain Dog Restaurant & Pub, loved by locals for its smashed burgers.

For those inspired by local craftsmanship, Main St. is your destination: Peruse the collections at Ledge Hill Studio, which frequently showcases regional artists, and find souvenirs at Bessboro Shop, a well-loved gift and clothing boutique. Stop by the Mill ADK for their latest art installment. Check of the Finishing Stone for locally crafted jewelry. Catch a matinee or reserve evening tickets at the Depot Theatre, an architectural gem and cultural beacon. This professional equity theater, housed in a historic train station, embodies the town's commitment to blending heritage with Adirondack ingenuity. 

Evening:  

Reserve a table at The Yacht Club, a lakeside venue that elevates farm-to-table dining with American-contemporary dishes. Pair your meal with selections from their thoughtfully curated wine list while the sunset casts a golden glow over Lake Champlain. Make room for a nightcap and bring your dancing shoes to The Mill, an arts center, jazz lounge, and plant-based speakeasy in an old flour mill, recently touted by The New York Times for bringing national acts into such a rural, intimate, and acoustically refined space.

Day 2: Outdoor recreation for the Adirondack adventurer  

Morning:  

Start the day on the Champlain Area Trails, where curated paths meander through verdant meadows and dense forests, offering opportunities for photography and quiet contemplation. For a touch of adventure, rent a kayak from the Westport Marina and paddle the tranquil waters of Lake Champlain, where the distant Adirondacks create a painterly backdrop. 

Afternoon:  

Lunch at Portside, located at the marina, offers American cuisine infused with a delightful Hawaiian twist, with many vegan, vegetarian, and gluten-free options. Dine al fresco to enjoy the lake breeze and watch the sailboats drift by.  

For golf enthusiasts, the Westport Golf Course, designed by Thomas Winton, provides a challenging yet scenic 18-hole course nestled among rolling hills. Worked up an appetite? The onsite tavern serves traditional “meat & potatoes” fare, delicious pub snacks, and a friendly happy hour!

Evening:  

It will be hard to choose: Spend your evening at Ballard Park, where curated weekly concerts and drive-in-style movie screenings run throughout the summer, or check the calendar for the chance at a private concert at the renowned Meadowmount School of Music. If schedules align, a world-class violin recital here is a treat not to be missed.  

Day 3: The agricultural landscape reimagined  

Morning:  

Fuel your morning at K&D Deli. Stop by for fresh coffee, fresh bakes, and the perfect breakfast to start your day right. Then, visit the Westport Heritage House, which doubles as a visitor center and an introduction to the region's agrarian past.  

Afternoon:  

Venture to DaCy Meadow Farm, a working farm that offers guided tours, showcasing sustainable practices and providing a fresh perspective on modern agriculture.

Conclude your day with a drive through the scenic landscapes of Essex County, where gentle hills and open farmland reveal the timeless charm of the Adirondack countryside.  

Travel Tips

Lodging: Stay at the Westport Inn, an independent inn in the heart of town or opt for a lakefront stay at the Lakeside Motel, impeccably clean and conveniently next to the town’s boat launch. There are also many vacation rentals offering privacy and a range of personalized luxury throughout Westport’s town, fields, and forests.
Culture: Westport prides itself on its intellectual and artistic community; many locals are involved in the arts or sustainable practices, making it a haven for engaging conversation and thoughtful exploration.  

Westport is more than a destination—it’s an invitation to step into a narrative where history, artistry, and nature converge. This serene little town promises not only a weekend retreat but also an invitation to return and explore more. Learn more and plan your visit at GoWestportNY.com.