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September 15, 2017
5 picturesque places to visit this fall in Boston
Uber Boston

Fall in Boston is iconic for its indescribable beauty. With summer coming to an end and autumn just around the corner, Boston locals and visitors just passing through are in for a real treat this season. Though you won’t see the leaves change colors or the golden-brown tint in the scenery just yet, that doesn’t mean you can’t start enjoying fall in Boston right away. Check out our list of top fall destinations in Boston and the surrounding area. 

What to do in Boston this fall


1. The Fells

Middlesex Fells Reservation, more commonly known as The Fells, is a massive recreational area just outside of Boston, covering sections of other nearby cities like Medford, Stoneham, Melrose, Winchester, and Malden. The best way to explore the 2,200-acre terrain is by hiking the Skyline Trail. True to its name, this famous trail gives way to breathtaking vistas and panoramic views of the Boston skyline.

Where: 4 Woodland Rd – Stoneham, MA


2. Fruit Picking at Boston Hill Farm

Boston Hill Farm is a famous destination for picking your own fruit. Their seasonal supply of apples in particular (and also strawberries, raspberries, blueberries, peaches, and pumpkins) draws droves of people looking for fresh fruit and family-friendly fun. Though the apple picking period is over, you can still collect peaches or get pumpkins if you’re so inclined. Go quickly, before the peach season ends.

Where: 1370 Turnpike St – North Andover, MA


3. Dogtown

Now a ghost town in Gloucester, Dogtown was, among other things, home to some of the infamous witch trials. The abandoned village is now a park with gorgeous greenery and trails worthy of hours of wandering. Bring a map when you visit and get ready for long, winding hiking trails like the Gloucester trail or the Babson Boulder trail. The ideal time for these trails is when you have a leisurely afternoon to spare as you marvel at one of the most beautiful natural landscapes in Boston.

Where: End of Dogtown Rd – Gloucester, MA


4. Freedom Trail

If you’re a history buff, there’s no better Boston attraction than the Freedom Trail. You can go on the excursion on your own or participate in one of the official walking tours hosted daily by the Freedom Trail Foundations. The 2.5-mile trail takes you through 16 notable locations that played a role in the American Revolution. A red brick line leads the way, starting at Boston Common, winding through downtown Boston, and ending at the Bunker Hill Monument.  

Where: 139 Tremont St


5. Visit Salem

Salem requires no introduction. The town is best known as the center stage of the Salem witch trials and has sparked national curiosity ever since. Because of its reputation, Salem is a New England touristic hotspot. When you visit, be sure to check out the Salem Witch Trials Memorial, the House of the Seven Gables, and the Peabody Essex Museum.

Where: Salem Witch Trials Memorial – 24 Liberty St – Salem, MA

House of the Seven Gables – 115 Derby St – Salem, MA

Peabody Essex Museum – 161 Essex St – Salem, MA


Whether you’re in the mood for historical thrills or adventurous sightseeing, there is no place like Boston in fall to enthrall you.

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Uber Boston