Summer 2021 Wolfeboro Activities - The Pickering House Inn

Staff Picks: Summer 2021 Activities In and Around Wolfeboro

Life is feeling almost back to normal here in Wolfeboro! Socially distanced boating, hiking and biking were popular activities in Summer 2020 — and outdoor activities will always be our claim to fame. But now some of those outdoor activities can be far less solitary, plus many indoor venues are opening up! The vast majority of the most popular Wolfeboro attractions will be open in Summer 2021 and a wide range of events are already on the books.  Here are a few of our top recommendations for guests staying at Pickering House Inn:

Millie B & NH Boat Museum Events — The NH Boat Museum  (NHBM) fulfills its mission to preserve and share the boating heritage on New Hampshire’s fresh waterways through a wide range of fun events, from weekly model yachting competitions to an annual vintage race regatta and vintage boat and car auction. A reservation on the Millie B — a 28-foot “woodie” — is a fantastic way to explore Lake Winnipesaukee and a “must do” for many of our guests. Visit

Music, Dining and Exploring at Castle in the Clouds –Castle in the Clouds in nearby Moultonborough is a mountaintop estate featuring a 1913 mansion, 5500 acres of hiking, amazing lake views from a dining patio and more. A full calendar of events is being offered in 2021. Visit

Outdoor Concerts — The Great Waters music series is back with an eclectic line-up of performers and a new venue at Castle in the Clouds. All concerts will be  under a tent that seats 500 people inside with additional lawn seating available. Visit

If you want to stay closer to Pickering House Inn, look no farther than Cate Park, located almost right across the street. At this writing, we are not sure the Cate Park band concerts will be offered in 2021, but we are crossing our fingers!

Fairs, Festivals and Special Events — Wolfeboro’s summer calendar is filling up fast with antiques & crafts fairs, outdoor flea markets, sidewalk sale days and more. Visit the events calendar at 

Weekly Farmer’s Market —  Located just a short walk up the street from Pickering House Inn,  the Wolfeboro Area Farmer’s Market is a fun way to sample local wares and catch some music. The farmer’s market is offered every Thursday from May 6 until October 28 from 12:30-4:30 pm. Learn more at

Museums — In addition to the NH Boat Museum mentioned above, Wolfeboro is home to the Wright Museum of World War II. The museum showcases the contributions made by World War II-era Americans both on the battlefields and at home. Learn more at

If natural history is more your thing, you won’t want to miss the Libby Museum, the oldest natural history museum in New Hampshire. Learn more at For a full list of museums in Wolfeboro, please visit the Chamber website.

This is just a sample of events and activities on tap for Summer 2021. If you are staying at Pickering House Inn, our Guest Services Team would be happy to share other options or put together an itinerary for your stay!