Sailboat on the Charles River in Boston, MA

I love the vibe of Boston in the early fall months. It’s still pretty active, the temps are cooler, and the colors are of course beautiful. I lived in the metro a few years back and recently planned a trip from my new location, Tucson, to visit a family member. We decided to plan a quick overnight stay in the city to stroll around the parks, visit a few of our favorite restaurants, and take a leaf peeping cruise. The Charles River is the perfect place to enjoy any type of recreation this time of year. I’ve always wanted to take a bike ride or walk along the riverfront path but haven’t gotten around to it yet.

We figured mid October would be a great time to enjoy the foliage. Unfortunately, this year was a bit of a bust but we did enjoy the cruise nevertheless. A leisurely afternoon cruise along this iconic river is the perfect laid-back way to take in all the historic architecture of both Boston and Cambridge. If you are not up for a long walk along The Freedom Trail, this is a great alternative to see some landmarks and learn more about the city. This 80 mile long river runs a picturesque 23 mile long course, from Hopkinton (a small town just 30 min outside of the city most well-known for being the starting point of the Boston Marathon) to the harbor.

The best place to sightsee

The Charles Riverboat Company offers a number of sightseeing cruise options during the summer and fall season. If you are interested in history and/or architecture, I definitely recommend booking your tickets. Along the way, you will pass many historic sights of interest including Harvard University, Beacon Hill, and the Massachusetts Institute of Technology. We learned a lot about the city and it was nice that our tour guide pointed out sights of interest, especially to those not familiar at all with the city’s history.

While there are a number of tour companies in the area, this one particularly stands out as you get to enjoy views of both Cambridge and Boston. Plus, the area is less congested, it’s easier to find parking, and cruise rates are much more affordable than others I’ve researched in the area.

Here are a few historical sights which our guide pointed out:

Fall foliage in Cambridge
Moors Hall at Harvard University
Dunster house at Harvard University
Dunster House at Harvard
One of the campus residence halls at MIT
Maseeh Hall – one of the residence halls at MIT

Leaf peeping cruises

The fall foliage cruises are most popular as New England is well-known for being the leaf peeping capital of the US. During my time living here, I hiked so many gorgeous trails. This time around, we were interested in observing the foliage in a different way as we were on vacation and didn’t want to work up a big sweat.

The historical architecture combined with the traditional hues of autumn really leads to some postcard-worthy scenery. While peak season typically falls around the 2nd or 3rd week of October, foliage can be a hit or miss depending on the year. Although we didn’t see all that much in terms of fall colors, we did enjoy the beautiful river and skyline views.

About the only foliage we saw the entire trip although our visit fell during typical peak season!

Hint of fall foliage along the Charles River

For comparison, this is what the foliage typically looks like in this area. This orange tree pic was taken at the same time of year a few years back on the beautiful Minuteman Bike path which connects to the Charles River path.

Brilliant orange foliage on the Minuteman Bike path

Fortunately, we still got to enjoy some architecture along the way, both historic and modern to keep things interesting. This is a strange city where hundreds of years old buildings stand next to modern architectural masterpieces.

The Clarendon, the largest building in Boston
The 200 Clarendon, formerly the John Hancock, is the tallest building in New England, at 790 ft.
Pretty views of Boston from the Charles River
Views of the Boston skyline from a Charles riverboat cruise

A great alternative to walking

In a busy tourist city, it’s nice to enjoy the scenery from afar without walking amongst the throngs of people. This is especially the case if you have visited the city a time or 2 before. As you kick back on the open air boat enjoying the lovely city scenery and fresh breeze, you will get to learn some historical facts via your tour guide. Complimentary snacks and apple cider, as well as a cash bar were available during our tour.

Seeing all the locals out and about enjoying the beautiful riverfront made me want to get out there. There are so many ways to get active here. It was hard but we were trying to skip any hefty exercise on this trip so maybe next time. We saw kayakers, rowers, paddleboarders, sailers, and bikers out enjoying the mild temps. After seeing all the fitness enthusiasts out and about, you may want to join in. The riverfront path is 23 miles so perfect for a long weekend of biking, jogging, or walking.

Sailing on the Charles River in Cambridge
The beautiful Charles River Bike path
The gorgeous 20+ mile long bike path – what a scenic place to bike, run, or walk!

More to do in Cambridge

Cambridge is just a quick drive or taxi ride downtown. It’s worth the detour if you have already seen all the usual tourist attractions and are looking for something new to do. This cruise is entertaining, scenic, and relaxing all at the same time, which is hard to come by in a busy city. I think it is the perfect vacation activity for anyone looking to relax. I love that you can park in the mall lot for under $5 bucks (really a steal compared to all the pricey lots).

While in the Cambridge area, I also recommend taking the fantastic, free tour of Harvard University. Not only will you get to take a walk around the school’s gorgeous grounds, but you will also learn a lot about the history of the school and local legends, and even get to enjoy a few interesting tidbits about campus life. We took a student led tour and it was great to get the inside scoop from those who actually attended. Most of all, I loved learning more about the Legend of the Statue of 3 Lies (you’ll learn more on your tour).

Widener library at Harvard University
Harvard’s gorgeous Widener library was dedicated by Eleanor Widener to her son Harry after his death in the sinking of the Titanic in 1912. You’ll learn this as well as many other interesting tidbits on the Harvard tour.

Where to dine nearby

When you get back to the city, there are of course tons of wonderful options for lunch. Check out Legal Sea Foods, which offers not only tasty seafood, but great views of the harbor. And if you are looking for something a bit more touristy and cultural, check out the Bell in Hand Tavern, the oldest pub in the country, located right in the middle of all The Freedom Trail action. They serve excellent seafood and offer great views looking out at the North End. Try the Fisherman’s Platter!

Bell in Hand tavern in Boston
The city’s oldest pub
Fisherman's Platter at Bell in Hand Tavern in Boston, Massachusetts
The Fisherman’s platter is loaded with fried shrimp, haddock, scallops, onion rings, and fries

Tickets and parking

Cruise options and booking

Parking is available at the Cambridge Side Galleria Mall at 100 Cambridgeside Pl.

Tip: Check Groupon for specials deals.