Things To Do
Freedom Trail
If you like history, this is a great option. You can pick a few locations, make it a walking tour, or take the trolley. Stop into America’s oldest continuously operating restaurant, Union Oyster House, located in Faneuil Hall. Established in 1826, it sits in a pre-Revolutionary building and is famous for its raw oyster bar, New England clam chowder, and classic seafood Fun fact: Faneuil Hall was one of the first places Melissa took Frank on his first trip to MA! Union Oyster House is where Frank enjoyed his first cup of Boston Clam Chowdah.
The North End
If you are looking for delicious Italian food, The North End is the place. Walk around the cobblestone streets, and warm up with authentic Italian food after your walk. Locals often recommend grabbing a cannoli at Bova's Bakery over the heavily tourist-trafficked Mike's Pastry if lines get too long. The Paul Revere House is also located in this part of the city (part of the freedom trail).
Charlestown, MA
Charlestown is Boston’s oldest neighborhood, blending rich Revolutionary history with a charming, brick-lined waterfront. Start by conquering the 294 steps of the Bunker Hill Monument, exploring the Charlestown Navy Yard to see the historic USS Constitution, and capping off the afternoon with a pint at Warren's Tavern—Massachusetts' oldest bar. Warren's Tavern used to serve Paul Revere and even George Washington! Fun fact: Melissa's paternal grandmother grew up in Charlestown!
Boston Duck Tours
This is a great way to see Boston from the water. There are three locations you can start at. Find parking and ticket information in the link.
Fenway Park
I think we can safely say the Red Sox won't still be playing this October, but that doesn't mean you can't still visit Fenway. Take a Tour of Fenway - or if you'd rather take a peek, you can enjoy a Sam Adams and lunch at Bleacher Bar, which is tucked into Center Field.
Acorn Street
Wander through the most photographed, cobblestone-lined streets in the country, which go all-out with fall foliage, pumpkins, and spooky stoop decor.
Salem
There is a lot to do in Salem in October if you're willing to fight the crowds. The Witch House: Tour the only structure still standing in Salem with direct ties to the 1692 Witch Trials Salem Witch Museum: Get tickets for a highly-rated presentation on the history of the trials and the evolution of the word "witch" Pioneer Village: Visit the 1630 living history museum, famous for being featured as Thackery Binx's village in the movie Hocus Pocus. Expert Tips: Book in Advance: October is incredibly busy. You must secure your museum and historic home tickets weeks—sometimes months—in advance. Parking: Parking is extremely limited. Consider parking for free at the MBTA Salem Commuter Rail Station or taking the Salem Ferry from Boston to avoid heavy traffic. Day-Of Tickets: Some popular experiences (like The Witch House or cemetery tours) only release their tickets on the day of the event, so check their sites early in the morning
Newburyport
Newburyport has a quaint New England downtown with shopping and restaurants overlooking the water. View the link to view restaurants and things to do.
Loon Mountain Resort
There is lots to do on the mountain, even in the off-season. Take a gondola ride to the top of the mountain and enjoy the Fall views. Your ikon pass will work to get you to the top.
Hikes around Lincoln, NH
The Fall foliage will be at its peak in early October. Grab your hiking shoes and take a hike to enjoy the vibrant colors of northern NH. Follow the link to find a hike that fits you best!
The Kancamagus Highway
The Kancamagus Highway - also known to locals as "the Kanc" is a spectacular 34.5-mile scenic byway winding through New Hampshire's White Mountain National Forest. Connecting Lincoln to Conway, the drive is famous for its panoramic mountain views, waterfalls, and vibrant autumn foliage. Follow the link to choose your stops along the way. Note: There are no gas stations along the way. The drive is about 45 minutes, but plan 2-3 hours, depending on how many stops you make.