Columbus Day is the first long weekend of the school year — let’s celebrate accordingly by getting off campus and out of the city! Struggle with planning? I have you covered from food to activities!
1. Portland, Maine
Distance from Boston: 114 Miles
Transportation: Amtrak or Car
Where to stay: The Cutest waterfront Airbnb
Portland is the hipster hub of New England, making it a unique place to visit (if you want to escape Ralph Lauren Polos & Nantucket red shorts). For the perfect date night, start with dinner at the Drifters Wife and finish with a romantic stroll along the eastern promenade. Other great restaurants include East Ender, Duck Fat, and my personal favorite (as a breakfast aficionado) Tandem Coffee and Bakery. In addition to the great food, Portland is buzzing with fun activities like The Portland Art Museum, Brewery Tours, and a visit to Cape Elizabeth. For a guaranteed 10/10 weekend head up to Portland! P.S. don’t forget to stop at Novare Res Bier for an extensive drink menu!
2. Manchester, Vermont
Distance from Boston: 163 Miles
Transportation: Car
Where to the Stay: The Reluctant Panther
I used to spend four weeks in Manchester every summer and I loved it. If you love Pancakes go to Up for Breakfast, a local institution. For a more upscale meal try the quiet and delicious restaurant at The Reluctant Panther. Lastly be sure not to miss Cilantro for a mind-blowing Mexican experience. My favorite part about Manchester is the endless options for things to do from hiking to shopping. Don’t miss the Manchester Outlets for great discounted stores. More into the outdoors? Take a hike, kayak amongst the fall foliage, or go apple picking! Pro-tip: don’t miss the apple cider doughnuts made fresh on Sundays at the Reluctant Panther.
3. Nantucket, Massachusetts
Distance from Boston: 100 Miles
Transportation: Car to Ferry or Airplane
Where to Stay: The Perfect Cottage
Most people think of Nantucket as a summer destination, but it can be just as beautiful (and significantly cheaper) in the early fall. Start with dinner at Cru before treating yourself to the best ice cream on the island. More a breakfast kind of girl? Don’t miss the opportunity to stop by Provisions. Visit the Chicken Box at night for great drinks & music as well! Even in the fall, you won’t be able to resist a stroll down one of the island’s beautiful beaches. If you are super ambitious, wake up to watch the sunrise at Brant Point Lighthouse. Love drinking beer? Don’t forget to stop by Cisco Brewers for a few samples. Nantucket is fabulous in the summer, but you can have an equally great time in the fall, trust me on this one.
4. Middlebury, Vermont
Distance from Boston: 187 Miles
Transportation: Car
Where to Stay: Swift House Inn
I love hard cider, it’s my absolute favorite drink and is my primary reason for adding Middlebury to this list. Stop by Woodchuck Cider for a tour and lots of tastings (personally it’s my favorite brand). Afterwards, don’t miss out on dinner at The Lobby. Revitalize the next morning with breakfast at the Storm Café or Rosie’s Restaurant. Don’t like cider? Visit the beautiful Morgan horses at the University of Vermont or book a spa appointment at the Woodstock Inn. More of a beer person? Partake in their Brewery tour too. You can also stop at one of Vermont’s famous covered bridges for the perfect Instagram. Of course, being a Lucy, I would be remiss not to recommend Lulu’s ice cream!
5. Bretton Woods, New Hampshire
Distance from Boston: 156 Miles
Transportation: Car
Where to stay: The Mount Washington Hotel
Bretton Woods is the ultimate romantic getaway (though of course it never hurts to have a girl’s weekend either). Enjoy a long & delicious dinner at The Mount Washington Hotel or head up the chairlift for dinner at Latitude 44 and enjoy dinner with a view. Want to have a drink or catch a sports game? Head to the Cave for the best of both. While NH isn’t known for its food, the activities are reason enough to make the trek. Play golf and tennis or mix it up and try the rock climbing wall! Of course, it also offers some of New England’s best skiing, though sadly not available by Columbus Day weekend. P.S. don’t forget to hike Mount Washington (jokes, but there are many beautiful and less challenging hikes in the area).