The Native American name for Lake Winnipesaukee means “Smile of the Great Spirit,” and it’s no wonder. Who could drive by this sparkling, spring-fed lake without breaking into a few grins along the way? Surrounded by three mountain ranges, the lake is the largest in New Hampshire with 178 miles of shoreline serving up nine lakeside towns and their respective attractions. And you can actually hit them all in one easy driving route, known as “The Lake Winni Loop Drive,” which travels 60 miles around the entire lake.
But rather than cram everything into one trip, we suggest you break it up over the course of a couple of days – one day dedicated to the eastern side of the lake, another on the western side. Here, our journey begins on the eastern side, starting in Alton Bay in the south and traveling through the many shoreline towns until you hit Moultonborough in the north.
The Route in a Nutshell: Start in Alton Bay and head north on NH Route 28t through the quaint New England town of Wolfeboro. From here, drivers will link up with NH Route 109 following this road through Tuftonboro. As you finally reach the opposite tip of the lake, stay left and continue along NH Route 109 into Moultonborough.
Pit Stop #1: Knights Pond [Alton]
Located just a few miles off NH-28, this scenic 31-acre pond is one of the few larger bodies of water in the Lakes Region without any development along its shoreline. That makes the 2.8-mile footpath around the pond one of the perfect places to catch glimpses of resident beavers, ruffled grouse, deer, as well as plenty of waterfowl.
Pit Stop #2: Downtown Strolling [Wolfeboro]
Known as “The Oldest Summer Resort in America,” the town of Wolfeboro offers a bustling downtown that can be hard to peel yourself away from. Located right along the waterfront on North, South Main, and Center streets, restaurants, boutiques, retail shops, and a slew of other businesses make their homes in 150-year-old colonial white-washed buildings. A few of our favorites: The Yum Yum Shop, a family-owned Wolfeboro staple for baked goods since 1948; the Wright Museum of World War II and New Hampshire Boat Museum, both celebrating the history of life on New Hampshire’s lakes; and Black’s Paper Store & Gift Shop, offering two sprawling floors of literally everything you could ever need (books, toiletry items, candy, toys, gifts, art supplies, sweatshirts, snacks, greeting cards, souvenirs, and so on). If looking to wet your whistle, Winnipesaukee Winery offers a patio and signature wine slushies.
Pit Stop #3: Cotton Valley Rail Trail [Wolfeboro]
Beginning at Depot Street in downtown Wolfeboro, this popular four-season trail extends 12 miles along lakes, woods, fields, wetlands, and historic train sites all the way to the neighboring town of Wakefield. While you won’t have time to stroll, bike, or run the whole trail, sweet amenities such as picnic spots, benches, and bridges over babbling brooks allow you the perfect spot to take a moment and just soak all the scenery in.
Pit Stop #4: Village Antiques & Classic Cars [Melvin Village]
What looks to be an old-fashioned pump station – lined by tall antique gas pumps (the kind where the gasoline was contained in clear glass cylinders) – is actually home to a car museum. Located in Melvin Village, a tiny town that is technically a part of Tuftonboro, the site is the permanent home of classic vehicles, including two rare models: a 1911 Franklin and a 1913 Model T.
Pit Stop #5: Castle in the Clouds [Moultonborough]
Before hitting the main village of Moultonborough and located on a mountaintop in the Ossipee Mountain Range sits this castle-like estate, boasting spectacular views of Lake Winnipesaukee. Originally built by a wealthy shoe-manufacturing mogul in the early 1900s, the stunning Arts and Crafts–style estate is open to visitors to learn about its history, roam through the gardens, enjoy a meal at one of the restaurants, go horseback riding, or stroll along one of the many hiking trails on property.
Pit Stop #6: The Loon Center [Moultonborough]
Located on the north shore of the lake on the grounds of the Frederick and Paula Anna Markus Wildlife Sanctuary, this headquarters for the Loon Preservation Committee houses public interpretive exhibits, presentations, and a gift shop all dedicated to educating and preserving the region’s iconic bird: the loon. A surrounding 200 acres of upland forests, marshes, ponds, clear-running streams, and more than 5,000 feet of pristine shoreline is where more than 10,000 yearly visitors gain a greater understanding of loons and the natural world.
Pit Stop #7: Moulton Farm [Meredith]
While technically just around the tip of the lake into what would be considered the western side of the lake, this farm market serves as the perfect end stop for your drive. Based in a 40- by 80-foot pole barn, the market sells scores of product freshly plucked in the farm’s surrounding fields, including corn, heirloom tomatoes, carrots, green and colored peppers, artichokes, pumpkins, and gourds. But come fall, it’s also the home base for Cider Bellies Doughnuts, where fresh, hot apple-cider flavored donuts are handmade right in front of you by Jessica Stephens (wife of Farm Manager Rob Stephens).
**Please confirm details with business/attractions prior to visiting due to possible restrictions.