How to Visit All 36 Wineries on the Connecticut Wine Trail in One Year

On a golden fall afternoon, you sip a glass of rosé overlooking rows of vines as the leaves begin to change. A couple nearby stamps their wine passports, laughing about how many more stops they have to go. That’s the charm of the Connecticut Wine Trail Passport Program—an invitation to visit all 36 wineries across the state in a single year.

Connecticut’s wine scene is growing fast. According to the Connecticut Farm Wine Development Council, the state’s vineyards bring in millions each year and attract visitors from across New England. With 36 wineries, the goal is simple: visit about three each month. This pace leaves time for small towns, farm stands, museums, and some of the best restaurants in New England.

Here’s a 12-month itinerary that blends wine, food, shopping, and seasonal fun—all mapped out so you can make the most of every trip.

Vineyards

Month-by-Month Itinerary

January: New Haven & Wallingford

• Wineries: Gouveia Vineyards (Wallingford), Rosabianca Vineyards (Northford)

• Eat: Union League Café (New Haven) – a French-inspired fine dining spot near Yale.

• Do/Shop: Tour the Yale University Art Gallery or browse the historic New Haven Green area.

February: Hartford Valley

• Wineries: Paradise Hills Vineyard (Wallingford), Brignole Vineyards (East Granby), Lost Acres Vineyard (Granby)

• Eat: Max Downtown (Hartford) – modern American cuisine in a sleek setting.

• Do/Shop: Explore the Wadsworth Atheneum Museum of Art and hunt for treasures at Collinsville Antiques Co.

March: Litchfield Hills

• Wineries: Hopkins Vineyard (Warren), Sunset Meadow Vineyards (Goshen), Connecticut Valley Winery (New Hartford)

• Eat: The White Horse Country Pub (Marble Dale) – classic New England tavern fare with high reviews.

• Do/Shop: Antique shopping in Litchfield and a nature walk at White Memorial Conservation Center.

April: Western Connecticut (Bonus Month – 4 Wineries)

• Wineries: Jones Winery (Shelton), Aquila’s Nest Vineyards (Newtown), Walker Road Vineyards (Woodbury), Tranquillity Vineyard (Middlebury)

• Eat: Good Old Days Pizzeria (Newtown) – wood-fired pizza with creative toppings.

• Do/Shop: Stroll through Woodbury’s antiques trail or visit Shepaug Dam to see bald eagles in season.

May: Mystic & Stonington

• Wineries: Stonington Vineyards, Saltwater Farm Vineyard, Jonathan Edwards Winery

• Eat: Oyster Club (Mystic) – award-winning seafood in a rustic-chic setting.

• Do/Shop: Visit Mystic Seaport Museum and shop the cobblestone paths of Olde Mistick Village.

  
  

June: Southeastern Countryside

• Wineries: Kingdom of the Hawk (North Stonington), Holmberg Orchards & Winery (Ledyard), Maugle Sierra Vineyards (Ledyard)

• Eat: Octagon at the Mystic Marriott – upscale steak and seafood.

• Do/Shop: Tour the Mashantucket Pequot Museum or shop handmade nautical gifts at Mystic Knotwork.

July: The Quiet Corner

• Wineries: Taylor Brooke Winery (Woodstock), Sharpe Hill Vineyard (Pomfret), Priam Vineyards (Colchester)

• Eat: 86’d (Pomfret) – a stylish, farm-to-table bistro.

• Do: Hike the Wolf Den at Mashamoquet Brook State Park, then wander through Putnam’s antique shops.

  
  

August: Shoreline & River Valley

• Wineries: Chamard Vineyards (Clinton), Arrigoni Winery (Portland), Staehly Farm Winery (East Haddam)

• Eat: Cafe Routier (Westbrook) – Mediterranean-inspired with a French twist.

• Do/Shop: Ride the Essex Steam Train, and browse Clinton Premium Outlets for shopping.

September: Hartford & Tobacco Valley

• Wineries: Crystal Ridge Winery (South Glastonbury), Worthington Vineyards (Somers), Heartstone Farm & Winery (Pomfret area)

• Eat: Carbone’s Prime (Rocky Hill) – Italian classics with a modern edge.

• Do: Explore Elizabeth Park Rose Garden in Hartford, one of the oldest public rose gardens in the U.S.

October: Peak Foliage (Bonus Month – 4 Wineries)

• Wineries: Hawk Ridge Winery (Watertown), Jerram Winery (New Hartford), Land of Nod Winery (East Canaan), White Silo Farm & Winery (Sherman)

• Eat: The Mayflower Inn’s Garden Room (Washington) – fine dining with seasonal menus and countryside views.

• Do/Shop: Drive scenic Route 7 for fall foliage and browse artisan shops in Kent.

November: Eastern Gems

• Wineries: Sunset Hill Vineyard (Lyme), Savino Vineyards (Woodbridge), Independence Vineyard (Lebanon)

• Eat: Shell & Bones Oyster Bar (New Haven) – upscale seafood with a harbor view.

• Do: Visit Lebanon Green, a Revolutionary War-era historic district, or shop local craft fairs before the holidays.

December: Holiday Cheer & Finale

• Wineries: Bishop’s Orchards Winery (Guilford), Rose Vineyards & Winery (North Branford)

• Eat: Griswold Inn (Essex) – one of America’s oldest inns, serving hearty New England fare.

• Do (Festivals):

  • Mystic Seaport’s Lantern Light Tours

  • Olde Mistick Village Festival of Lights

  • Niantic Light Parade

  • Essex Steam Train’s North Pole Express

  • Hartford Holiday Light Fantasia drive-through

Tips for Making It Work

• Plan smart: Three wineries per month keeps things fun and easy.

• Time it right: Summer brings outdoor concerts; fall means foliage and farm stands.

• Travel with friends: It’s safer, more fun, and easier for sharing driving duties.

• Explore fully: Pair each winery stop with meals, shops, or museums for a well-rounded adventure.

Enjoying red wine

Visiting all 36 wineries on the Connecticut Wine Trail isn’t just about collecting passport stamps—it’s about discovering the hidden treasures of New England. With great wine, charming small towns, farm-fresh food, and unforgettable festivals, every trip becomes a story worth telling. Are you ready to grab your passport, raise your glass, and see how far the trail can take you?