The Freedom Trail is probably the most popular tour of Boston. It will take you on a 2.5 mile walk through the old red-brick streets of Boston, connecting 16 nationally historic sites (including museums, churches, meeting houses, burying grounds, parks, a ship, and historic markers) that illustrate the story of the American Revolution. You will start at the Boston Commons and end at the USS Constitution. Be prepared to spend the full day on the trail if you decide to stop at all historic sites.

The Black Heritage Trail is a short city walk with a very rich history focusing on the emancipation of the African American community over the 19th century. The sites that you will see on your walk include houses of worship, homes, schools, museums and memorials that will take you back in time and allow you to learn about the Black community’s longtime fight for equality and justice through the Abolition Movement and the Underground Railroad. Relax after the walk at nearby Philips Street Park.

World’s End is a peninsula that is part of Boston Harbor Islands National Recreation Area. It is a haven for hikers and riders alike looking to escape the bustling city for a day. World’s End Trail will offer you panoramic views over the Boston skyline, Hingham Harbor, and Weir River, whether under a sunny summer day or snowy winter afternoon. It is also home to an amazing biodiversity including tree-lined paths, tree groves and wide grassy fields that provide habitat for butterflies and birds.

Deer Island belongs to Boston Island National Recreation Area and can be accessed by car or public transportation. The Deer Island Trail is the best way to explore the island with your family and furry companions, by foot or on a bike. Enjoy a beautiful walk along the ocean with stunning views over the city, bay, the beaches, wildflowers, and a glimpse at the water treatment plant for the curious.

Boston’s Emerald Necklace is a network of trails, green spaces, and roadways that connect Boston Common to Franklin Park. It was designed by Frederick Law Olmsted and gets its name from the shape and orientation that it takes, similar to a neck to the Boston area. This trail can be hiked, run or cycled entirely or partially over several days or just a half day. Along the route, enjoy a visit to the Swan Boats, the Rose Garden, Fenway Victory Gardens or the Arnold Arboretum.

The Blue Hills Skyline Trail is a challenging trail that crosses the Blue Hills Reservation and is located only minutes away from the city. It is a green oasis made of forests, meadows, marshes, swamps, ponds, hills and rocky summits that offer rewarding views. It is quite a popular spot for Bostonians to hike or even run. The reservation is home to a variety of wildlife including snakes, deers, coyotes, foxes, turkeys and vultures, so keep your eyes open while on the trail!

Take a tour through the grounds of the oldest and one of the most prestigious universities of the United States! This Harvard Yard Tour is a self-guided walking tour that will allow you to admire the beautiful monuments and academic buildings on campus as well as to learn more about the rich history of this Ivy League School built in 1636. Don’t hesitate to stop at one of the museums on Quincy Street to complete your visit!

Immerse yourself in the fascinating history of the United States. The Battle Road Trail crosses Minute Man National Historical Park, connecting historic sites, remnants and monuments from the famous Battle of April 19, 1775, which marked the beginning of the American Revolution. The best way to explore the park on this paved path is definitely on a walk or bike ride. You will cross the forests, fields and wetlands of the Battle, preserved for visitors by the National Park Service.

Be ready for some breathtaking panoramic views! The Wachusett Summit Loop is a popular trail that goes to the summit and around Mount Wachusett, the highest peak of Massachusetts east of the Connecticut River. After reaching the summit, the hike will take you through some beautiful forests, meadows and ponds in a loop through Wachusett Mountain State Reservation. For an unforgettable adventure, we recommend hiking it during the fall foliage.