Port71, A Blog by Rockport

Travel Shoes and Such

Fall for Massachusetts’ Fall Destinations


Fall is one of our favorite times here in New England, not only for the fab footwear we get to wear, but also for the fantastic fall foliage and local festivities we are lucky enough to enjoy. Here are some of our top spots to visit in our hometown of Massachusetts this season, and a few fall shoes to help you stay comfortable while you’re here.


Shelburne Falls, Massachusetts: Experience some of the most beautiful foliage Fall has to offer in the quaint town of Shelburne Falls. Folks come from all over to leaf peep and view the Bridge of Flowers, a former trolley track turned gorgeous garden, housing over five hundred different varieties of perennials and annuals, from late spring to early fall. Another must-see: the Glacial Potholes, a collection of over fifty whirling pools left by the glacial age, over 14,000 years ago, and the site of the largest natural pothole on record. While you’re there, be sure to check out old town treasures like the Shelburne Falls Bowling Alley – one of the oldest in the country – and Gould’s Maple Sugarhouse for a pancake breakfast with local maple syrup. To see the sights in style and stay comfortable all day long, we suggest our Thurston Moc Boot for the guys and our Cobb Hill Willa Bow Slip On for the ladies.


Pictured: Thurston Moc Boot ($140) | Cobb Hill Willa Bow Slip On ($130)


Salem, Massachusetts: The old and historic town of Salem is a great place to visit year-round but truly comes to life in the fall. Check out Haunted Happenings for attractions and events, including guided tours, theatrical performances, haunted houses and hayrides. If you’re looking to learn about the famous Salem Witch Trials of 1692, the most popular attraction is the Salem Witch Museum, featuring exhibits with live narrations and guided tours. You can also stop by the House of the Seven Gables, the country’s oldest wooden mansion, and the inspiration for Nathaniel Hawthorne’s 1851 novel. While you’re walking around the ‘’haunted neighborhood’’ of the Salem Witch Village, be sure to wear comfortable shoes like our Colle Mid Lace Up and our Ariell Lace to Toe, both of which offer removable Ortholite® footbeds for lightweight, breathable cushioning. In black, perhaps.


Pictured: Colle Mid Lace Up ($125)| Ariell Lace to Toe ($90)


Boston, Massachusetts: Fall is one of the best times of the year to visit Boston, when the air is crisp and cool and the city is alive with festivities. One of the biggest events, The Head of the Charles Regatta, brings the world’s best crew teams to Boston, this year on October 21st– 22nd.  From beer and food to film and art, there seems to be a festival for everyone this time of year in the city. Check out Sam Adams Octoberfest for beer, live music and a stein hoisting competition, or Pumpkin Palooza at the Lawn on D for some Halloween-themed fun for the whole family. For a dose of colonial history, take the famous Freedom Trail Walking Tour. It’s 2.5 miles long so be sure to wear comfortable kicks like our Colle Slip On and our Cobb Hill Willa High Top.


Pictured: Colle Slip On ($120) | Cobb Hill Willa High Top ($140)

Find more comfortable styles for your next Massachusetts adventure for men & women here.

Shop This Story