If you decide to fly into Boston and have a few days to spare, we urge you to make a few pit stops before your final destination of Wiscasset. Here’s our list of noteworthy cities and towns of varying sizes, with some highlights for each. Note that we haven’t yet had the time to visit each and everyone town, so the below is a compilation of our research, not our experiences.
Boston, MA – the quintessential New England city, this is a can’t-miss for anyone who has never been. The options are endless. For history buffs, there is the Freedom Trail, Boston Tea Party Ships and Museum, and the JFK Presidential Library and Museum. If the weather is nice, be sure to check out the impeccably-manicured Boston Common or Boston Public Garden. For great people watching, don’t forget Newbury Street, North End, or Faneuil Hall/Quincy Market. And for those sports fans flying into or out of Boston, consider catching the home team take on the Yankees (8/9-11) or D-backs (8/14) at Fenway Park, the historic ballpark that inspired our MLB mini helmet collection.
Portsmouth, NH (57 miles north of Boston) – we’ve been dying to visit this little seaside town that is known for being the third oldest city in our nation. The NYT compiled a great “36 Hours in Portsmouth” article highlighting the artsy boutiques, galleries, breweries, and cafes lining the beautiful harborfront.
York/Ogunquit, ME (10/20 miles north of Portsmouth) – offers kayaking, parasailing, and scuba diving adventures along with a nice beach at York Harbor Beach. Go on the Cliff Walk to appreciate 19th century architecture, then cross York Harbor’s Wiggly Bridge, the smallest suspension bridge in the world. Be sure to stop by the iconic Cape Neddick Lighthouse (aka “Nubble Light”), one of the most photographed lighthouses in the country. In Ogunquit, enjoy the white sand beaches with natural dunes or go for a hike at Mount Agamenticus.
Kennebunkport, ME (10 miles north of Ogunquit) – this fashionable seaside port is also the summer home to our 41st President. Check it out at Walker’s Point, or take a walk or ride along nearby Ocean Avenue for its shops and restaurants. There’s plenty of beach and coastline to explore with kayaks or a lobster tour. And if the weather’s bad (or if you’re traveling with the tots), check out the Seashore Trolley Museum, where you can actually ride restored rail cars.
Portland, ME (30 miles north of Kennebunkport) – so awesome it deserves its own post. So it got one. Check it out here: Portland.
Freeport, ME (15 miles north of Portland) – if the outdoors isn’t your thing and you would prefer to exercise your wallet, try some outlet shopping at Freeport Village Station. Or, if the outdoors is your thing, come anyways and take a course at L.L. Bean’s Outdoor Discovery School from the company’s flagship store.
Wiscasset, ME (28 miles north of Freeport) – you’ve arrived at our wedding town! Check out some local activities on our Wiscasset page.