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Plan your perfect fall weekend in Massachusetts
Fall travel and apple-picking recommendations for Boston, North Shore, South Shore, and more.
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Welcome back to Scenic Six. The mild weather this week is fantastic, but it won’t stop the first day of fall from arriving on Monday. And, really, do we want it to? Fall is such a magical time in New England and this week I’ve rounded up plenty of ways to enjoy the season.
Also, find out how to snag a huge discount on “Hamilton” tickets in Boston this fall season and learn the eerie story behind a “Cursed Brick” featured in a Boston tour launching this week.
Plan your perfect fall weekend in Massachusetts
If your fall goals in the Bay State include picking apples, leaf peeping, dining out, hiking, and exploring lighthouses and historic homes, I’ve got you covered. Check out many great fall itinerary options for both the North Shore and the South Shore.
Here’s your family-friendly New England apple picking guide
Speaking of apple picking, families of little kids searching for farms with a focus on kid-centric fun this season (think scavenger hunts, storybook hayrides, and petting zoos) can plan their excursions with help of this family-friendly guide to apple picking in New England.
Discover the story behind the ‘Cursed Brick’ on this Boston tour
Someone stole a brick from the crypt of Boston’s famous Old North Church and then mailed it back after experiencing “a string of bad luck.” Now the “Cursed Brick” is on display during the church’s guided After-Hours Crypt Tour, launching this week. I spoke with Emily Spence at Old North Illuminated about the stolen brick and why it’s “cursed.”
Travel Tips
- Head to the 27th Annual Mount Snow Oktoberfest, happening Oct. 4 and 11 in Dover, Vermont for live music, beer, food trucks, games, and activities for all ages. Looking for other things to do in Vermont this fall? Check out eight reader-recommended spots.
- New England is full of delicious fall food festivals, so here’s how to eat your way through everything from Somerville’s What the Fluff? Festival to New Hampshire’s Laconia Pumpkin Festival.
- For those eyeing winter trips, North Conway, N.H. and Ludlow, Vermont are great mountain getaways on a budget this winter, according to TravelAwaits. North Conway was named the best ski town in North America by USA Today readers last year.
Deals and Steals
- If you long to be in the room where it happens, enter a digital lottery for a chance at $10 tickets to see “Hamilton” at Citizens Opera House in Boston Sept. 23 to Nov. 2. Forty discounted tickets will be made available for every performance and those interested must use the official “Hamilton” app to enter.
- Play a game of free miniature golf at USS Constitution Minigolf in the Charlestown Navy Yard. Each of the nine holes features fun facts about the United States Navy. The activity is open daily through the end of October.
- When travelers stay at The Pell in Middletown, R.I., part of the JdV by Hyatt collection, they’ll get two free tickets to The Breakers, the famous Gilded Age mansion in Newport. The offer code is 78439 and is valid through Jan. 31, 2026.
Discover how to save more money during New England travel in September.
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I’ll leave you with this photo of early signs of fall in Boston, taken by Jack.
Where have you traveled lately? Please share your photos by sending them to [email protected] and they may be featured in an upcoming Scenic Six newsletter.
Whether you’re traveling this week or planning your next escape, enjoy the journey.
— Kristi
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