6. Minuteman Bikeway

Bright orange fall foliage along the Minuteman Bikeway near Boston,

This Rail to Trails Conservancy Hall of Fame recipient is well worth the short drive from Boston. The route, an easy, scenic 11 mile journey through a mostly forested setting, is a great place to enjoy a healthy burst of weekend morning exercise. The path is very flat, one of the easiest in the area. I have been biking so many trails since moving to the region (seriously there are so many great options) and this is one of my favorites.

I really love biking this trail in autumn – seriously some of the best foliage I’ve seen anywhere. The tree-lined route passes through 4 historic Massachusetts towns: Bedford, Arlington, Lexington, and Cambridge. Any history buffs out there might find it interesting that the path closely follows Paul Revere’s Revolutionary ride. I can’t recommend this trail enough, both for history buffs and nature enthusiasts.

Gorgeous foliage along the Minuteman bikeway in Boston
Bright fall foliage along the Minuteman Bikeway in Boston

Tip: Those looking for a longer ride can continue on by connecting to various other paths such as the equally scenic Charles River path.

7. Old North Church

Old North Church on Boston's Freedom Trail

One of the most beautiful sights along Boston’s Freedom Trail is Old North Church, built in 1723. While there are many gorgeous churches in the city, Old North is the oldest church still standing in the city. However, it is most well-known for being the location from which the “one if by land, two if by sea” signal was sent by Paul Revere. The interior features unique architecture and box pews which are all original. Free admission to tour the beautiful interior is available, although $3 donations are suggested.

Tip: Special tours of the Crypt and the Bell Ringing Chamber are available for a small fee.

8. Middlesex Fells Reservation

View of the Boston skyline from the Skyline Trail at Middlesex Fells Reservation

Another great natural park just outside of Boston is Middlesex Fells Reservation, located just a short 10-15 minute drive north of the city. The skyline trail provides outstanding views of the city. Here, you can really escape the hustle and bustle as the trails are very peaceful, scenic, and opportunities for small wildlife sightings are abundant. Get out of the city and enjoy a day exploring nature at Middlesex Fells.  A variety of trails to suit all levels are available, with views ranging from forests to city to wetlands to ponds.

Hiking at Middlesex Falls near Boston
The hiking trails here are so woodsy and secluded

Tip: Plan a full day hiking trip to complete the entire Skyline Trail. It is a difficult trail, however, the views are stunning. Be sure to come prepared with plenty of water, a few snacks, and sunblock.

9. Salem Witch Trials Memorial/Old Burying Point Cemetery

Pretty fall views at Old Burying Point Cemetery in Salem, Massachusetts

Salem is most famous for being home to the infamous witch trials of 1692. While in town, you can take a walk around and view the 20 granite benches, commemorating each of the accused/executed. Next to the memorials, you will find Old Burying Point Cemetery, the oldest burial ground in Salem and one of the oldest in the US.

At this historic cemetery, you will find the gravestone of Judge John Hawthorne of the Witch Trials. Because this cemetery is so old (built in the 1600s), many of the gravestones are weathered down, and thus, no longer legible. It is a very creepy place, especially during the fall and winter months where overcast skies and barren trees make for an especially eerie feeling!

Salem Witch Trials Memorial
Witch Memorial
Old Burying cemetery in Salem
The graves are so old!

I love visiting in October when colorful fall leaves surround all the historic sites. Really visiting Salem during the autumn season is a dream for leaf peepers, history buffs, and Halloween fans alike.

Tip: Salem tends to get insanely crowd during the fall/Halloween season. I recommend visiting outside of October if you are not big into Halloween. On the other hand, if you love Halloween like me (and Hocus Pocus), you will want to check out my guide to Halloween fun.

Hocus Pocus house in Salem, Massachusetts
90’s kids will definitely want to plan a self-guided tour of Hocus Pocus filming locations!

10. Faneuil Hall Marketplace

Faneuil Hall on Boston's Freedom Trail

In 1742, Wealthy merchant Peter Faneuil funded the building of this marketplace and meeting hall. Many important figures such as Samuel Adams have made speeches here. Today, the marketplace is home to numerous shops, restaurants, bars, live events, and performances. There are always lots of crazy street performers here to keep things interesting.

In terms of food, you can enjoy a bit of everything in the country’s largest food hall. While I am kind of sad that the Cheers replica and Hard Rock closed, you can still enjoy local seafood eateries, the iconic Ned Devine’s Irish pub, and FoMu a wonderful local dairy-free ice cream shop.

Tip: Be sure to check out Blink! A Light & Sound Extravaganza, a synchronized holiday light show featuring Holiday Pops music. Takes place each December.

Read more about the history of Faneuil