Fall Weekend on Lake Winnipesaukee

By Richard Adams Carey

In 1763, New Hampshire Governor John Wentworth built a summer home on the shores of a lake whose name—in one translation from the Abenaki—means “Smile of the Great Spirit.” That home was in the village of Wolfeboro, which on that basis claims the title of “The Oldest Summer Resort in America.” But it never had to be summer for Lake Winnipesaukee to be a destination. Try it during New England’s fall foliage season, when all the local businesses are still bustling, and the vast lake and its surrounding mountains—the Belknap, Squam, Sandwich, and Ossipee ranges—are never more beautiful.

We’ll start in Wolfeboro, where Mitt Romney keeps a second home. Main Street runs the length of the waterfront, and if you stay at the Pickering House Inn on Main, you’ll find yourself in the newly—and immaculately—restored Federal home of Daniel Pickering, one of the town’s leading citizens in the 1800s. Innkeepers Peter and Patty Cooke offer gourmet breakfasts, sunny rooms that blend the historic and the contemporary, and a wraparound porch overlooking lush gardens, the campus of Brew­ster Academy, and Wolfeboro Bay.

A 10-minute stroll down Main brings us to Lydia’s Café, where the French toast comes heaped with tiny wild blueberries, sandwiched with cream cheese, and dolloped with whipped cream. Right next door is Made on Earth, a fair trade–certified boutique where natural-fiber women’s clothing is complemented by herb teas, scented smoke bundles, fine jewelry, and shelves of books on Eastern spirituality.

Through mid-October, the 205-foot M/S Mount Washington plies the lake daily between Wolfeboro, on the east shore—and past some of Winnipesaukee’s 300-plus islands—to Laconia’s Weirs Beach on the west. “The Weirs” once hosted a dance hall where the likes of Duke Ellington and Count Basie played; today its boardwalk hums with shops, restaurants, a tavern, a penny arcade, and the bump-bump of bumper cars.

If a proper car is handy, drive into Laconia for lunch at Trillium Farm to Table, a bright café that partners with local organic farms in its offerings. Wine, craft beers, and hard cider are available, but for a different take on a nonalcoholic fruit drink, try a cantaloupe shrub.

Your car will also prove handy for the 77-mile loop of roads around the lake and linking its towns. To the north of Laconia lies Meredith, where the League of N.H. Craftsmen keeps a shop stocked with unique handwrought items made with as much artistry as craft. At the heart of the town lies Mill Falls, with its 40-foot waterfall and an elegant array of shops, restaurants, and lakeside lodgings. Keep going north on Route 25 to the Moulton Farm stand: sustainable agriculture, a corn maze and pumpkin patch, and apple cider doughnuts as light as croissants.

Center Harbor, at the lake’s north end, was a favorite haunt of poet and abolitionist John Greenleaf Whittier. It was also the site of America’s first intercollegiate sporting event: the Harvard-Yale regatta of 1852. Winnipesaukee is surrounded by excellent restaurants, but Canoe is my choice today—say yes to the lobster mac and cheese, or the sweet-and-sour calamari—and is as lakeside as the Mount Washington. The Sutton family estate once dominated Center Harbor, and today the Suttons’ refurbished Victorian mansion is a homey B&B beautified by a Lisa Nelthropp mural of town history.

We begin to round back to Wolfeboro through Moultonborough, where the Old Country Store & Museum dates back to 1781. Its floor space and shelves are jam-packed with vintage and contemporary items recalling that name-it-we-got-it ethos of, well, old country stores. Then turn down Route 109 toward a jewel hidden high in the Ossipee Mountains: Castle in the Clouds, which began as Lucknow, a 6,300-acre estate and mansion—no, castle—built in 1913 by shoe magnate Thomas Plant. The builder eventually ran out of luck and went broke, but his restored home provides a window into the human spirit, a taste of a bygone opulence, and magnificent views south over the lake and north to the Sandwich Range.

Maybe you prefer to go on foot to where bald eagles soar. Drive through Wolfeboro down to Alton Bay, the lake’s southern tip. Go four miles up Route 11 to the trailhead for Mount Major. A moderate, hour-and-fifteen hike will reward you with a vista no less stunning than Mr. Plant’s. You’ll know how he felt, because you might want to stay forever.

Guide to Lake Winnipesaukee

Where to Eat

Canoe, Center Harbor: Five dining areas and a three-season porch with lake views to enjoy while tucking into lobster mac and cheese, among many other offerings. canoecenterharbor.com

Laconia Local Eatery, Laconia: Dogs are welcome at outside tables at this upscale farm-to-table establishment where all food (organic whenever possible) comes from within 140 miles. laconialocaleatery.com

Lydia’s Café, Wolfeboro: A small café with an outsize following for its all-day breakfasts, especially pancakes and omelets, as well as lunch. Facebook

Moulton Farm, Meredith: A garden center, a farm stand, a bakery, and an array of homemade foods to take home, all on land farmed since the 1890s. A corn maze and a pumpkin patch round out the all-in-one outing. moultonfarm.com

Trillium Farm to Table, Laconia: Supplied by nearly a dozen local farms and breweries and even a mustard maker, this Middle Eastern/Mediterranean-inspired eatery is one of the prime lunch and dinner spots in the region. trilliumnh.com

Yum Yum Shop, Wolfeboro: A local bakery landmark for seven decades whose signature frosted gingerbread men, doughnuts, pastries, and ice cream have linked generations of sweet tooths. yumyumshop.com

Where to Stay

Ames Farm Inn, Gilford: A low-key family resort on 135 acres on Winni’s southern shore, with its own quarter-mile beach. Open through Columbus Day Weekend. amesfarminn.com

Ballard House Inn, Meredith: At this c. 1784 inn, views of lake and mountains and homemade country breakfasts are enhanced with complimentary wine sipped while sitting on the backyard swing. ballardhouseinn.com

The Inn at Mill Falls, Meredith: Part of a cluster of four inns that helped revive Meredith as one of the main destinations in the Lakes Region, this one is dog-friendly, with designated doggie trails, pet beds, and a treat bag. millfalls.com/stay/the-inn-at-mill-falls

Long Island Bridge Campground, Moultonborough: Sites for RVs, trailers, as well as pop-ups and tents within a stone’s throw of Winnipesaukee. Canoe and kayak rentals available. Open till mid-October. longislandbridgecampgroundnh.com

Pickering House Inn, Wolfeboro: A now-restored c. 1813 local landmark, this 10-room inn is made for sitting on the porch overlooking the bay. pickeringhousewolfeboro.com

Sutton House B&B, Center Harbor: A pet-friendly Victorian mansion featuring nine guest rooms within a six-minute walk of Lake Winnipesaukee, which you’ll want to take after your sumptuous homemade breakfast. sutton-house.com

Wolfeboro Inn, Wolfeboro: The historic Wolfeboro Inn comes with its own private beach on Lake Winnipesaukee and a pub serving New England comfort food alongside upscale options and an extensive beer list. wolfeboroinn.com

Things to Do

Castle in the Clouds, Moultonborough: Autumn is made for chasing views, and one of the best in the Lakes Region is seen from this c. 1914 mansion perched on a mountainside. Tour the estate, and stroll its miles of walking trails. Through October 22. castleintheclouds.org

Mount Major, Alton: The summit of the 1,786-foot mountain provides a stunning photo op—colorful forest, expansive lake, and islands—via a 1½-mile hike that suits everyone. forestsociety.org/property/mount-major-reservation

Mount Washington Cruises, Laconia: The M/S Mount Washington departs from Weirs Beach daily and offers a grand tour of Winni, stopping at five ports along the way. Sunset dinner and scenic specialty cruises. Through mid-October. cruisenh.com