Under 1 Hour:
Newburyport, MA and Plum Island
Time: 50 Minutes
Newburyport is a seaside town filled with shops and great restaurants. While you’re there, you can head over to Plum Island to get in some beach time at either Newbury Beach or the Sandy Point state reservation (parking at either is around $10). I’ve been to Newburyport multiple times, as have my roommates, and we all agree that it’s definitely worth a trip.
Rockport, MA
Time: 55 Minutes
Rockport is a beautiful and historic town in northern Massachusetts. It has shopping, beaches, a harbor, and paths through the woods surrounding the town. Rockport is a great place to escape Bentley for the day to go explore a new place.
1-2 Hours:
Portsmouth, NH
Time: 1 Hour 10 Minutes
Another seaside town similar to Newburyport, but with its own flair. Portsmouth is a great place to head for a day trip, but be prepared to do some walking. They also have a great park right on the water. There’s tons of great shops, restaurants and cool photo ops. Portsmouth is a town where you can find something new every time you visit and is a great day trip to make. In the spring and summer, you can also take cruises around the harbor.
Ogunquit and York, ME
Time: 1 Hour 20 Minutes
Both Ogunquit and York are seaside towns in Maine just farther north than Portsmouth. Both have great shops. York is home to The Goldenrod, a candy store and restaurant. If you head to Perkins Cove in Ogunquit, you can walk around the scenic harbor, take a harbor cruise, or walk down the Marginal Way: a seaside pathway with beautiful views. Be sure to try food from The Lobster Shack while you’re there. Also, if you do this trip, make sure you stop by the Cape Neddick Lighthouse (aka Nubble Light) right outside York. This lighthouse is one of the most photographed lighthouses in the country and is definitely worth a stop. I took this trip a few weeks ago with my roommates and we loved it!
Newport, RI
Time: 1 Hour 30 Minutes
Newport is the seaside town in Rhode Island home to the well-known Newport mansions, such as The Breakers, The Elms, Marble House, Rosecliff, and more. These huge, Victorian homes were built by some of the richest families in America as their “summer cottages” and look like they came straight out of The Great Gatsby (in fact, the original movie was filmed partially at Rosecliff). You can drive by or walk through the estates and take tours of the magnificently decorated homes. Also, the town of Newport has shops that you can visit, but the main reason to go is most definitely the mansions. (For a closer version, try Castle Hill in Ipswich, MA).
Mount Monadnock, Jaffrey, NH
Time: 1 Hour 30 Minutes
For those who like to hike, Mount Monadnock is a great mountain you can head to that’s relatively close to Bentley. There are a variety of trails of varying difficulty that you can choose from, so be sure to do some research and grab a trail map before you go (you can print one online). On a nice day, you can see great views from the summit.
Doane’s Falls, Royalston, MA
Time: 1 Hour 15 Minutes
If you’re not up for a full hike up a mountain, you can try Doane’s Falls. Once you arrive, to get to the falls you have to walk along a half mile trail next to the stream to the woods. There’s also another trail that leads to a meadow. The falls are a series of cascades on the Lawrence River that are the most popular group in their region of Massachusetts.
2-3 Hours:
Provincetown, MA and Cape Cod
Time: 1 Hour 30 Minutes- 2 Hours 20 Minutes
While it’s definitely not a winter trip, a visit to Cape Cod is something you should definitely do at least once. There are great towns to visit all along the Cape. Provincetown is an especially cool place to visit; it’s the town all the way out on the tip of the Cape. While it might be a bit of a hike for a day trip, a long weekend in Cape Cod with friends would be a great mini vacation.
Kancamagus Highway, White Mountains, NH
Time: 2 Hours 20 Minutes
This is the ideal trip to take during the fall, as you can see all the beautiful fall foliage that New Hampshire’s White Mountains have to offer. Driving through this mountain pass, you can see beautiful views from the highway and scenic overlooks. There are also stops on the sides of the highway where you can go on short hikes or sit and picnic by the Pemigewasset River. While you’re in the area, you can also take a drive through Franconia Notch or stop at Lost River Gorge and Boulder Caves. There are plenty of restaurants in the area that serve great food you can get while you’re up there, like One Love Brewery in Lincoln or Woodstock Inn Brewery in North Woodstock.
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