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Exploring Boston in the Fall

September 13, 2021

Fall is that incredible time of year when the temperatures drop, the stunning autumn foliage comes to life, and when our lively city of Boston is truly at its best. Whether you’re looking for a day trip to an apple orchard, or something more local, like enjoying a seasonal craft beer, we’ve curated a list of festive activities to make the most of one of the most anticipated seasons of the year.

Apple Picking

Fresh, crisp apples taste even better when you pick them yourself! Escape the city for the day and head to one of the several farms and apple orchards that reside just outside of Boston. Less than a 40-minute drive from The Overlook, you’ll find Lookout Farm, Honey Pot Hill Orchards, and Brooksby Farm. What apple-inspired treats will you bake up in your fully-equipped Overlook kitchen?


Boston is home to some of the most gasp-inducing fall foliage in the country. Before the city turns gray for the winter, getting out and enjoying the vibrant colors of yellow, orange, and red is a must. So, head just outside your door and explore the gorgeous scenes of Brighton at Fidelis Way Park and Ringer Park, or head about 15 minutes away to some of the top leaf-peeping spots in the city, including The Public Garden, Boston Common, and The Esplanade.

Indulge in a Cider Doughnut

Aside from leaf-peeping, one of the biggest New England autumn traditions is treating yourself to a crispy, golden-brown cider doughnut! Just 3 miles from The Overlook, you’ll find some of the best cider donuts in the city at Blackbird Doughnuts, or travel a little further and find the beloved treat at Red Apple Farm, located about 5 miles away at the Boston Public Market.

Pumpkin Patchin’

One of the best fall activities has to be visiting a pumpkin patch and picking out the perfect gourd for a Halloween jack-o-lantern. Lucky for us, we’re just a day trip away from some of the most incredible farms in Massachusetts. Including Allandale Farm, about a 15-minute drive away, and the popular Pakeen Farm, about a 30-minute drive away from The Overlook.

Head to the Brewery

What better way to spend a crisp fall afternoon than sipping a cold one with your favorite people at some of Boston’s best pubs and breweries? Find one-of-a-kind beers

and ciders close to The Overlook at Trillium, offering some of the most highly prized drinks in the city, or check out the Night Shift Brewing Owl’s Nest in Allston. Both are located about 2 miles from our community.

The Overlook at St. Gabriel’s Fall Festival

You’re invited to The Overlook at St. Gabriel’s Fall Festival happening Saturday, September 25th! Festival-goers will have the opportunity to shop local vendors, including Espresso Dave, Something Bespoke Ice Cream, Lume Lux, White Marz Farm and Rocco’s in Millbury. You can also compete in a friendly cornhole competition, stroll through a pumpkin patch, indulge in fall-flavored drinks and treats, enjoy an acoustic performance and so much more. We hope to see you there!


The possibilities for having a festive fall season are endless when you live at our conveniently located Brighton apartment community. Start living the life you were meant to lead when you schedule your tour of The Overlook at St. Gabriel’s today.

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