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Carving Out a Great Time: 10 Must-See Autumn Spots to Visit in Boston

Autumn in Boston: Could there be anything more picturesque or beautiful?

“Tourists flock to our city and the surrounding areas each fall to enjoy the glory of autumn leaves, taste the fresh-pressed apple cider, get spooked by our history and celebrate the onset of the holiday season,” says Jake Quigley, Executive Director of Waterstone at the Circle. “There are so many unique-to-Boston sights, smells, tastes and sounds that should definitely be on your must-see list this autumn.”

We’ve compiled some of our favorite spots to visit when the leaves turn in our fair city. Even though COVID-19 regulations are still in place, all of the spots and sights we’ve listed are open to the public (with restrictions). Before you head off on any adventures, however, we suggest visiting websites or calling locations to triple check availability.

Now, grab your checkered flannel, strap on your boots and grab your knitted cap – fall fun is waiting.

Leaf Peeping

1. Boston Common, the first public park in the United States, has some of the oldest trees in the city and they explode in beautiful fall colors each autumn. It’s a wonderful place to stroll, rest on benches and relax by the picturesque Frog Pond.

2. Next to Boston Common is the Public Garden, the country’s first botanical garden and an absolute delight for taking in the fall foliage. The wide array of different trees and shrubs burst into color at different times during the season, creating an ever-changing array of hues.

3. Few things are more picturesque than walking along the Charles River Esplanade when the leaves turn. The best foliage is rumored to be on the stretch between Berkeley Street and the Charles River Dam Road, but anywhere you look will be worth the view.

4. If you’re more of a “scenic drive” type of peeper, hit the Mohawk Trail – a 69-mile stretch of road along Route 2. It’s considered to be one of the most beautiful scenic drives in Massachusetts. Along the way, you’ll see the tree-covered Berkshire as well as the Mohawk Trail State Forest. Along the route are easy-to-access scenic viewpoints, gift shops, roadside attractions and other points of interest.

Ghoulish Fun

5. Ghosts and Graveyards of Boston has long been a draw for ghost hunters and thrill seekers, and during the Halloween season, the Old Town Trolley's Ghosts & Gravestones Tour is a can’t miss. The 90-minute tour winds its way through Boston’s most sordid past, chilling and thrilling spectators with tales of the Boston Strangler, Jolly Jane, Cotton Mather and others. The Ghosts & Gravestones Halloween Tour is another local favorite for those over the age of 13.

Get Lost in the Best Possible Way

6. If corn mazes are your thing – do we have a treat for you. The Marini Farms Corn Maze has long been hailed as the best corn maze in the area, with eight acres of trails carved through thousands of living cornstalks. It’s not your typical corn maze, either – it’s interactive and informative as well as fun. Eighteen stations are strategically placed throughout the maze, and it’s your goal to find each one of them. You don’t get clues or a map – it’s up to you to find your way through the maze on your own (helped along by the “game sheet” you receive at the beginning of the maze). After you’ve hiked the stalks, visit the farm stand and bakery for delicious treats and fresh produce.

Pick a Pumpkin or Two (or Apples)

7. Russell Orchards was planted in 1920, and 100 years later, the orchard is a destination for anyone in the Massachusetts area. With 120 acres of fruits and vegetables, a bakery, a winery and a gourmet gift shop, it’s a great place to spend a relaxing fall day. While wine tastings and  certain parts of the barnyard have been closed off to the public for now, you can still gather handfuls of delicious apples for your home pantry.

8. Honey Pot Hill Orchards is well-known for its 200 acres of orchards, fresh pressed cider (a new batch is made every Friday) and their world-famous cider donuts. Reservations are required for pick-your-own visits – be sure to check the site for the most up-to-date information.

9. The historic Hanson’s Farm has been offering “pick your own” pumpkin experiences for generations, and is a family tradition for many Bostonians. The farm also offers haunted hayrides and a corn maze that is open to the public until November.

Wade Through a Cranberry Bog (Updated for 2020)

10. Apples are good, but cranberries are where it’s at. Cranberries are one of Massachusetts’ primary exports, and every fall, visitors strap on waders and boots and slosh through cranberry bogs for a uniquely Massachusetts experience. While many farms have canceled tours this year, some are still open – and others have their stores open so you can still get a taste of the cranberry experience. Visit the Massachusetts Cranberries site for information on what bogs are open, who’s offering tours and re-opening information.

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