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Scenic 5-Day Lake Ossipee Getaway Itinerary

Last updated: 2024 Jun 14

Lakeside Serenity and Local Flavors

Morning

Begin your Lake Ossipee adventure with a serene morning by the water. Enjoy a delightful breakfast at River's Edge Grille & Tavern, where you can savor the morning calm with a view of the lake. After breakfast, take a leisurely stroll along the Lake Ossipee shoreline, breathing in the fresh mountain air.

Afternoon

For lunch, head to Indian Mound House of Pizza for a casual meal with a local touch. Post-lunch, indulge in some watersports at Squam Lake, just a short drive away. Whether it's kayaking, paddleboarding, or simply lounging on the beach, the afternoon is yours to enjoy the crystal-clear waters.

Evening

As the sun sets, treat yourself to a dinner at Hobbs Tavern & Brewing Company, known for its hearty brews and comforting dishes. After dinner, take a scenic drive to catch the last light at Mount Washington Observatory Weather Discovery Center, where you can learn about the unique weather patterns of the region.

Bedtime

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Mountain Views and Culinary Delights

Morning

Wake up to the aroma of fresh coffee at Dunkin', a New England staple. Grab your favorite brew and head to White Lake State Park for a morning hike. The easy trails offer beautiful views of the surrounding mountains and the chance to spot local wildlife.

Afternoon

After working up an appetite, drive to Jake's Seafood & Grill for a classic New England seafood lunch. Post-lunch, continue your culinary exploration with a visit to Sap House Meadery, where you can learn about and taste the region's unique meads.

Evening

Dine at The Wooden Spoon, a cozy spot known for its farm-to-table fare. End the evening with a visit to Windy Fields Farm, where you can take a guided tour and interact with the friendly alpacas.

Bedtime

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4.56
Sap House Meadery
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Historic Journeys and Scenic Drives

Morning

Start your day with a hearty breakfast at MountainView Station, a charming spot with a view. Post-breakfast, drive to Castle in the Clouds in Moultonborough. Explore the historic mansion and gardens, and don't miss the stunning views of Lake Winnipesaukee from the mountaintop.

Afternoon

For lunch, enjoy the laid-back atmosphere and delicious pizzas at Pizza Barn. Afterward, take a leisurely drive along the Kancamagus Highway, one of the most scenic routes in New England. Stop at the various viewpoints and take in the beauty of the White Mountains.

Evening

As the day winds down, head back to Lake Ossipee for a dinner at Deb's Landing, a local favorite for its waterfront dining. Afterward, take a relaxing evening cruise on the lake with Lake Ossipee Cruises, where you can enjoy the peaceful waters and the company of loons.

Bedtime

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Kancamagus Highway
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Nature's Bounty and Local Crafts

Morning

Enjoy a breakfast with a view at Windy Fields Farm, where you can savor farm-fresh ingredients. Post-breakfast, visit Libby Museum in Wolfeboro to learn about the natural history of the area, including the famous Ossipee Lake ring dike.

Afternoon

For lunch, head to Ossipee House of Pizza for a quick bite. Spend the rest of the afternoon exploring the quaint shops and galleries of Downtown Wolfeboro, known as the "Oldest Summer Resort in America."

Evening

Dine at Yankee Smokehouse, where you can enjoy a hearty meal in a rustic setting. After dinner, indulge in some retail therapy at The Loon Center and Markus Wildlife Sanctuary, where you can find unique gifts and souvenirs while supporting local conservation efforts.

Bedtime

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Farewell to the Lakes and Peaks

Morning

Have a final breakfast at Harley Jacks Burgers and Brews, fueling up for the day ahead. After breakfast, take a scenic drive to the summit of Mount Washington, the highest peak in the Northeast. Experience the "Home of the World's Worst Weather" and enjoy the panoramic views.

Afternoon

Descend from the mountain and enjoy a well-deserved lunch at Blue Sky Restaurant & Bar in North Conway. Afterward, explore the charming village and its many outlets, shops, and galleries, or take a ride on the Conway Scenic Railroad for a leisurely journey through the valley.

Evening

As the trip comes to a close, reminisce over a farewell dinner at Flatbread Company, known for its delicious wood-fired pizzas and commitment to local, organic ingredients. Raise a glass to the memories made in the White Mountains and Lake Ossipee.

Bedtime

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