Salem is directly next to Peabody, Massachusetts where our wedding is being held. It is a very walkable city with plenty to do, eat, and see. For restaurants, I would recommend making a reservation to avoid waiting. Prior to October, parking is much easier. Here is the parking information for Salem.
Boston is a very scenic and walkable city with so much to do. While you can drive into Boston, I would recommend parking outside the city and taking the commuter rail in to avoid traffic and high parking fees. Once in the city, buying a ticket for the Old Town Trolley Tours lets you hop-on and hop-off for the day if you'd like a tour but don't feel like walking everywhere.
If you have time, I recommend driving along the Kancamagus Highway which is a portion of NH Route 112 spanning east to west from Lincoln to Conway in New Hampshire. The 34.5-mile drive is a recognized National Scenic Byway, offering travelers rich history and natural beauty in addition to being considered one of the best fall foliage viewing areas in the world. Depending on the year, NH typically has plenty of fall foliage by mid-late September.
Cape Cod is a picturesque destination known for its beautiful beaches, charming villages, and maritime history. About a 2.5 drive from Salem, Cape Cod. Around the time of our wedding, visitors can enjoy fall scenery, attend events like the Wellfleet OysterFest, and engage in activities such as biking the Cape Cod Rail Trail or whale watching from Barnstable Harbor. Post-Labor Day is considered off-season, so you typically won't need to pay to park at the beaches. I also recommend taking the ferry to Martha's Vineyard or Nantucket. Watch the weather though, because if a storm rolls in, the ferry might not run.