The Perfect Romantic Labor Day Weekend in Stonington, CT
A Couple’s 3-Day Romantic Itinerary in 2026
If you are spending Labor Day weekend 2026 at the Inn at Stonington, you have chosen one of the most romantic inns along the New England coastline in New England to slow down, get outside, and enjoy the Connecticut coast.
My advice is simple: do not try to see everything.
Let the Inn at Stonington be your home base and build your weekend around the things that make Stonington special: water, history, wine, golf, beaches, and walking.
Friday: Arrive, Unwind and Explore Stonington Borough
After checking into the Inn at Stonington, take some time to enjoy your room and its amenities.
Many of the Inn’s 18 individually decorated rooms feature harbor views, private balconies, soaking tubs and gas fireplaces.
The Inn also provides complimentary Wi-Fi and parking.
Then put on your walking shoes and explore Stonington Borough.
Walk along Water Street, admire the historic sea captain homes and stroll toward the Stonington Lighthouse.
Historic Stonington’s museums offer a wonderful introduction to the community’s maritime history.
Return to the Inn at Stonington in time for the complimentary wine and cheese reception from 6 to 7 p.m.
Grab a glass of wine, relax overlooking the water and watch the boats move through Stonington Harbor.
Then enjoy a marvelous dinner within walking distance of the Inn at Stonington.
Saturday: Golf, Wine and the Connecticut Coast
Start Saturday with the Inn at Stonington’s complimentary continental breakfast, served from 8 to 10 a.m.
Golfers can spend the morning at nearby Pequot Golf Club, a convenient choice for a round close to Stonington.
After golf, head to Stonington Vineyards for an afternoon of Connecticut wine.
Labor Day weekend is particularly appealing because Stonington Vineyards has live music and food vendors scheduled for September 5, 6 and 7, 2026.
For a second vineyard experience, consider Saltwater Farm Vineyard, located in Stonington.
Return to the Inn at Stonington for the evening wine and cheese reception, followed by dinner and a leisurely walk along the harbor.
Sunday: Kayaking, Fishing and the Beach
After breakfast at the Inn at Stonington, make Sunday your water day.
Rent kayaks or paddleboards and explore the quiet coastal waters around Stonington.
The Inn specifically recommends local kayaking and paddleboarding options, including King Cove Marina and NESS.
If fishing is more your style, consider arranging a charter from the local marina.
For something less ambitious, simply spend some time watching the fishing boats and working waterfront around the Borough.
Later, walk to the small Borough Dubois Beach.
Note: If you plan to visit Sandy Point (the small island off of Stonington Point, passes must be purchased through Rhode Island National Wildlife Refuge Complex.
The Inn at Stonington provides complimentary beach chairs, towels and umbrellas for guests, making an afternoon by the water particularly easy.
Come back to the Inn at Stonington, freshen up and enjoy a complimentary wine and cheese hour before dinner.
Monday: One Last Walk Before You Leave
Enjoy your final complimentary breakfast at the Inn at Stonington, then take one last walk through the Borough.
If you missed them earlier, visit the Lighthouse Museum or Captain Nathaniel B. Palmer House, both important pieces of Stonington’s maritime history.
Before checking out, take a few minutes to sit by the water and enjoy what makes the Inn at Stonington so romantic.
The beauty of this weekend is that you do not need to rush.
Golf in the morning, wine in the afternoon, history on foot, salt air by the water and a glass of wine at the Inn at Stonington each evening.
For a couple who loves the outdoors, history and the coast, it’s the perfect romantic Labor Day weekend.
We look forward to your visit!
Sue, Stephanie and Bill
