The Best Three City Day Trips from Boston

The Best Three City Day Trips from Boston

As part of a new post series, we’ve decided to make a list of the best three city day trips from Boston, MA. Since Boston is in such a prime New England location, there are plenty of good day trip options. The day trips we’ve compiled all involve seeing three cities in one day with less than four hours of roundtrip drive time. They are perfect for the busy traveler and definitely get you the most travel “bang for your buck”. If you prefer a slower pace, cut out one of the options and make it a two-city trip instead.

Our first day trip combines lighthouses, lobsters, and L.L. bean. What could be more New England?!

1) Portland, ME; Freeport, ME; and York, ME

Total roundtrip driving time: 4 hrs.

Start your morning with driving from Boston to Portland, ME. This drive will take about 1.5 hours. Upon arriving in Portland, head straight to the holy grail of donuts, Holy Donut. These donuts are made from fresh Maine-grown potatoes. They have flavors such as maple bacon, Maine apple, and blueberry. The donuts are perfectly doughy and just the right amount of sweet.

Chocolate coconut and Maine apple

Holy Donut has 2 locations in Portland: 7 Exchange Street and 194 Park Avenue. I recommend heading to the Exchange Street location because it’s in the Old Port area of town. After waiting in line for your donut (it moves quickly), walk down to the waterfront and find a bench to enjoy your new favorite treat.

After devouring a couple of donuts, walk around the Old Port area for a bit. This area is known for its 19th century red brick buildings and cobblestone streets. It’s lined with shops, restaurants, and bars. You can also head over to the Eastern Promenade for a morning stroll. It’s a paved walking and biking path that weaves along the water.

Next, it’s time for some beer! Portland is known for its great craft beer. I recommend driving over to Allagash Brewery for a tasting. See my recommendations and reviews below:

Your Guide to Breweries in Portland, Maine

If you aren’t ready to get back into your car after Allagash, the industrial park area has plenty of other breweries (Austin Street and Foundation Brewing). I’ve written about those in the above linked post as well.

Allagash gives each visitor a free flight! They also have a great patio area.

Before your next stop, you may be hungry. I would recommend grabbing a slice of pizza at OTTO pizza. This New England chain was founded in Portland and is known for its high quality and unique slices. My favorite is the potato, bacon, and scallion.

This pizza speaks for itself.

If you feel like you can spare some extra time in Portland, I highly recommend driving over to Cape Elizabeth to see the Portland Head Light. It is known as the most photographed lighthouse in the U.S. and it is truly a stunning view. There is plenty of free parking around the lighthouse and you can walk throughout the grounds. There is even a small museum on site.

Portland Head Light on a beautiful summer day.

Next, drive up to Freeport (about 30 minutes from Portland). When in Freeport, you have a few options. The first option is to continue your brewery exploration and head to Maine Beer Company. This is one of my favorite breweries due to their high quality beer and ecofriendly attitude. I have written all about my experience there in the above Portland brewery guide so check out that post for beer recommendations!

Another option is to check out the L.L. Bean headquarters. Have a photo shoot in front of their massive ”Bean boot” and do some shopping. Keep in mind that all L.L. Bean products have a lifetime warranty. Can’t beat a good investment!

After Freeport, drive about an hour to York, ME. The “Maine attraction” here is the Nubble Lighthouse. You can drive right up to Nubble and there is a good-sized parking lot. Time it right and get there when the sun is about to set. Spend an hour or so watching the sunset and getting some great photos (which probably won’t do it justice).

Nubble at sunset!

From York, you will have a little over an hour drive back to Boston.

The second featured day trip combines mansions, a metropolitan, and a mill town. Check out the itinerary for a fun-filled day:

2) Newport, RI; Providence, RI; and Pawtucket, RI

Total roundtrip driving time: 3 hrs. 10 mins.

From Boston, head straight to Newport, RI (around 1.5 hours drive). When you get to Newport, stop by Empire Coffee & Tea for a to-go caffeinated drink of choice. Then, head to the Cliff Walk for a beautiful morning stroll. Park at Ocre Point (near the Breakers mansion) and walk for a couple of miles, checking out the extravagant mansions and craggy cliff views along the way.

Stunning views along the cliff walk.

When you pass the Breakers mansions on your way back, stop in and have a look. The Breakers is the “summer cottage” of the Vanderbilt family. Definitely not quaint, it has a total of 70 rooms designed in the Italian Renaissance style. A ticket to enter the Breakers costs $24 per adult and can be purchased online in advance. If you do purchase your ticket in advance or purchase a pass to multiple mansions, you can skip the long line in the front, which is for people that do not yet have tickets.

The beautiful Breakers mansion all dressed up for the holidays!

After dreaming of being a Vanderbilt in a past life, head back to your car and make your way to Providence. This drive will take about 40 minutes. Head up to the College Hill neighborhood of Providence to check out Brown University’s beautiful campus and get some incredible views of the State House.

After all this walking around, you’re probably getting hungry. Head over to Federal Hill, which is Providence’s Italian neighborhood. Atwell Avenue is lined with Italian restaurants. There are plenty of good options on this street for some good pasta or pizza including Enoteca Umberto. After your lunch or dinner, walk over to Pastiche Fine Desserts for some cake or a pastry.

Leaving Providence full and happy, drive about 10 to 15 minutes to Pawtucket. Pawtucket is definitely not beautiful. It kind of has the old, abandoned mill town feel. But what it lacks in beauty, it makes up for in quality beer. There are several breweries in Pawtucket that we highly recommend.

Crooked Current Brewery is female-brewed small batch beer in varieties such as Oatmeal Cookie Stout or Neapolitan Brown. The beers are amazing but they do have very limited hours so check the website.

We also recommend Bucket Brewery and Foolproof Brewing Company for a tasting. These breweries have more traditional style craft beers but are still high quality.

All breweries mentioned have parking available.

After a responsible amount of beers, you will have about a 45 minute drive back to Boston.

Our third recommended day trip combines frights, fun beaches, and fishing ports. Check out the itinerary below:

3) Salem, MA; Rockport, MA; and Gloucester, MA

Total roundtrip driving time: 2 hrs. 40 mins.

From Boston, drive about 45 minutes to Salem. The home of the Salem Witch Trials, there is plenty to do and see in this cute little town. We recommend parking your car (there’s plenty of street parking and affordable lots) and walking around. Grab breakfast at the historic Red’s Sandwich Shop, which is located in the former historic London Coffee House from circa 1698. It’s cash only so make sure to stop at the ATM.

Red’s Sandwich Shop. Get the pancakes!

From there, take a stroll down the pedestrian only Essex Street and make your way to the Salem Witch Trial Memorial & Burying Point. The memorial has a tribute to every victim that was hanged (or pressed) as a result of the brutal witch trials. The graveyard has some famous residents, including a pioneer that come over on the Mayflower ship. After wandering through the historic graveyard, walk down to the picturesque Salem Wharf for some really nice views.

From Salem, get on the scenic route 127A to weave your way to Rockport. This coastal drive is absolutely gorgeous. You’ll drive through Beverly and Manchester by the Sea (popularized by the recent movie). You’ll see some beautiful cliff views and huge houses along the way. This scenic route will take about 45 minutes but is so worth it.

You’ll have to stop along the way because you’ll see views like this.

In Rockport, walk down the touristy Bearskin Neck where you’ll see some cute shops and lobster shacks. Stop for a coffee and pastry at Helmet’s Strudel. They have some tables and chairs out back on their patio with a beautiful view of the water.

If you want some beach time, head to Front Beach, which is a small but scenic beach in the middle of town. It’s also a really nice place for a picnic if you’re so inclined.

Leaving Rockport, backtrack about 5 miles to Gloucester. Since Gloucester is famous from the show Wicked Tuna, you’ve got to get some good seafood while you’re here. Our favorite place is the Causeway Restaurant. It’s not a fancy place, but the quality of the seafood is so worth it. Also, the portions are massive so we recommend splitting a couple of dishes. After dinner, head to Cape Ann Brewery for a beer and some nice views of the harbor.

From Gloucester, you’ll have about an hour drive time back to Boston.

Happy road-tripping and, as always, happy picnicking!

-Kristin

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