100 Things to do in New England
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New England is one of my favorite areas of the country that I’ve lived in. I love the mix of recreational, entertainment, historical, and educational attractions. I love that I can be in a big city exploring museums one minute, and then walking down an old-fashioned Main Street the next. Whether you are into history, sports, photography, great dining, or the outdoors, you will have such a wide range of attractions to consider. Massachusetts, Rhode Island, Connecticut, New Hampshire, Maine, and Vermont all have one thing in common: beautiful natural forested lands. This is by far the most gorgeous area I have lived in and I love the dramatic change of seasons.
I have lived in Massachusetts for several years and had the opportunity to explore so many wonderful places. I love how you can get to so many different states so quickly. As you will see, many of my favorite places in New England include those which provide both scenic views and a great workout, most of the time at no cost! After numerous years living in the region and many vacations, I have compiled a guide of just some of my favorite things to do. Note that this list is not all inclusive as I have not traveled as extensively through Maine, Vermont, and New Hampshire. Part 2 will be coming soon!
1. Walk the historic Freedom Trail
Boston’s famous 2.5 mile journey takes you on a self guided journey through 16 sights of historical significance, from America’s oldest park, Boston Common, to the USS Constitution in Charleston. A brick pathway guides you in the right direction. You will want to bring the camera along as you will pass some of the country’s oldest cemeteries, amazing architectural wonders, beautiful parks, and historical landmarks. A trip to Boston is not complete until you journey back in time along the Freedom Trail. I like walking this trail most in winter – it’s so quiet and I can really explore without competing with tourists.
My guide & handy map to exploring the Freedom Trail
Location: 139 Tremont St, Boston, MA 02108 (Starts at the Boston Common Visitors Center)
2. Take in gorgeous ocean and mansion views along Cliff walk
The best views in Newport can be enjoyed via a 3.5 mile oceanfront path known as Cliff Walk. This stunning walk is conveniently located just behind the famous mansions, nonetheless, often overlooked by tourists who simply do not know that this wonderful, free attraction even exists. Fortunately, a family member who has lived in the area for over a decade told us about this gem. This breathtaking walk features spectacular views of both the ocean and the mansions. You will see many opulent mansions along the way, the most prominent being the extravagant 70 room Breakers at a whopping 125,000+ square feet! If you only have time for one Newport attraction, this is bar none the one to pick in my opinion.
Location: Cliff Walk, Newport, RI 02840
3. Hike the Mt. Battie trail at Camden Hills State Park
My favorite part about living in Maine was hiking this amazing little state park located on the Mid Coast. Camden Hills is home to over 30 scenic hiking trails, including the iconic Mt Battie trail. After a moderately tough climb of a half mile, you will get to enjoy stunning views of Penobscot Bay and the surrounding mountains. Camping, picnicking, and winter sports such as snowshoeing and cross country skiing trails are also available within this 5500 acre park. Tip: A hiking stick comes in handy for this hike as well as any others in the area.
- Location: 280 Belfast Rd, Camden, ME 04843
- Check out the full trail guide
4. See the Red Sox play at iconic Fenway Park
A visit to Boston would not be complete without catching a Red Sox game at historic Fenway Park, the oldest ballpark in America. 2012 marked the 100 year anniversary! Every fan should experience sitting in the Green Monster (the nickname given to the 37 foot tall left field wall) section at least once! Despite being a Chicago native, I have always been a fan of Boston sports. I am a huge Patriots fan and always wanted to see a Red Sox game since seeing the movie Fever Pitch. If you love the Red Sox and really Boston in general, I recommend watching this romantic comedy with Jimmy Fallon & Drew Barrymore. And, yes, the whole crowd really sings Sweet Caroline during the 8th inning home games! Read the story behind the tradition.
Location: 4 Yawkey Way, Boston, MA 02215
5. Take a picturesque ocean view hike at Sachuest Point Wildlife Refuge
Sachuest Point is my favorite park in the Newport area to hike. Not only do you get to enjoy quaint views of the coast, but it is also a beautiful birdwatching and wildlife watching destination. My favorite trail, the 2.5 mile Ocean Loop, features peaceful ocean and marsh views. After Cliff Walk, it ranks as the 2nd best place to take a nature walk in Rhode Island in my opinion. The best part of all is that most tourists are busy at the mansion and beaches, so you basically have the trails to yourself (along with a few locals). Be sure to pack a camera! Deer sightings are very common, unfortunately so are ticks (I actually found one on Mike’s neck), so be sure to check yourself after your hike! Check out the many bird species found within the park!
Location: 769 Sachuest Point Rd Middletown, RI 02842
6. Ride the tree-lined Minuteman Bikeway (in the fall)
One of Massachusetts’ top bike paths, the Minuteman Bikeway, runs north of the city from Bedford to Cambridge along the route of a former railroad. The 10 mile paved path is flat, well-marked, and tree-lined for the entire route. Fall is an incredible time to visit; in fact, some of the best fall foliage in the area can be spotted along this gorgeous trail. Out of all the fall hikes and bike rides I have enjoyed in the state, this is by far my favorite. I’ve never seen so much gorgeous fall color all in one place. I totally recommend a walk or bike ride here if you love leaf peeping.
Location: 110 South Rd Bedford, MA 01730 (starts at the historic Bedford Depot)
7. Spend a day exploring Plymouth’s Waterfront
As you walk along the quaint Plymouth, MA waterfront, you will come across 2 iconic attractions: the Mayflower replica and Plymouth Rock. You will also come across a number of waterfront dining options, including local seafood and Italian options. Mamma Mia’s is a fantastic local gem offering a big menu of Italian specialties, great service, and a beautiful outdoor terrace. Also, Plymouth is a fabulous destination for whale watching. I even found a bit of seaglass at the town beach. Overall, this is one of my favorite summer coastal destinations.
Read my guide to exploring Plymouth’s waterfront
Location: Water St. Plymouth, MA 02360
8. Ice skate amidst a snow globe setting at Nestlenook Farms
If you ever wondered what it would be like to step inside a snow globe, skating while surrounded by a snowy mountain range, now is your chance! Jackson, New Hampshire’s Nestlenook Farms resort is an absolute winter fantasy for ice skating, from the chime bells and horse drawn carriage rides, to the snow capped mountains surrounding the rink. Skating here is about as close as you can get to stepping inside a Hallmark Christmas movie! This 3 acre Victorian rink provides a perfect setting for holiday and winter recreation. As someone who has been ice skating for more than 10 years, I have yet to find a more charming rink.
Location: 66 Dinsmore Rd, Jackson, NH 03846
9. Take a hike through Devil’s Hopyard State Park
One of Southeastern Connecticut’s most beautiful parks is oddly named Devil’s Hopyard (the origin is unknown but likely due to a local legend of the devil stomping). Photographic opportunities await you at every turn, from beautiful Chapman Falls (a 60 foot waterfall surrounded by trees) to a historic covered bridge. This park offers the perfect fall New England setting – hundreds of trees, striking autumn colors, ponds and streams, and leaves scattered amongst the trails. It’s even more stunning during the peak of all (but really, the sames goes for every park in the region). I’ve never seen a more postcard worthy fall hiking destination – you really cannot top seeing a gorgeous covered bridge and waterfall surrounded by orange and yellow leaves.
Location: 366 Hopyard Rd, East Haddam, CT 06423
10. Enjoy a Whale watching cruise
Massachusetts ranks among the best places in the world for whale watching. Plymouth, a beautiful harbor town, is the perfect place for a spring or summer whale watching adventure. Sightings on the Captain John’s cruise are guaranteed – a major bonus to anyone who has previously been disappointed on tours. Don’t worry though; we saw plenty of whales during our trip. I also loved the scenic views of the harbor almost as much as seeing the whales. We learned so many facts about whales and the history of the city too. Tip: Discount deals can often be found on Groupon.
Location: 10 Town Wharf, Plymouth, MA 02360
