Massachusetts, Rhode Island & Connecticut

In effort of getting to all 50 states, my husband and I made plans to road trip through New England, while living in the North East. With other trips planned, we didn’t have a consecutive 7-10 days that we could take away from work. Therefore, we decided to do our road trip in 2 parts, over Memorial and Labor day weekends.

With Memorial Day being in May, just the start of summer in the North East, we decided to do the southern half first and follow up with the northern half in August. 

Both times, we rented a car and started and ended our road trip in Boston. We flew in, early Friday morning, and spent the day in Boston. Check out my blog post “2 DAYS IN BOSTON OR THE START TO YOUR NEW ENGLAND ROAD TRIP” to see how we spent our time there. The following day we got up early, grabbed a coffee, and got on the road- headed to Rhode Island. 

Plymouth Rock

On our way to Rhode Island we made a stop where the Pilgrims did when they first came to America; Plymouth Rock. We spent about a half an hour walking around the small town. We had originally planned on checking out Mayflower Brewing Company but unfortunately it wasn’t opened yet so we continued on to Rhode Island. 

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Newport, Rhode Island

Newport, Rhode Island is a popular place for summer weddings; with that being said, Kevin and I had trouble finding a place to stay within Newport so we opted for an AirBnB in Tiverton,RI. 

Tiverton is only 14 miles from Newport but takes about 30 minutes to get there. We were happy to stay there because the AirBnB that we stayed in was very cozy and was only 10 minutes from Carolyn’s Sakonnet Vineyard. Kevin and I spent most of the early afternoon enjoying the beautiful weather while wine tasting. We didn’t stay there late enough but our host mentioned that the winery has live music on summer nights. 

After the vineyard, we made our way to Newport to check out what all the fuss was about, and we were not disappointed. Before we really started exploring the town, we stopped for some New England Clam Chowder from The Black Pearl.

“Clam chowder at Black Pearl is the dish every visitor should try, because it’s a classic, one of a kind, and an unshakable part of Newport’s cultural heritage.”

Newport is a small coastal town, with beautiful mansions that are open to the public. Have you ever been to the Biltmore in Asheville, North Carolina? Think that times 8. While I believe the Breakers is the most popular, they also offer tours of The Elms, Marble House, Rosecliff, Chateau sur Mer, Isaac Bell House, Kingscote, Chepstow, Hunter House and Green Animals Topiary Garden. If you want a closer look at the water and views that these homeowners get to see daily, visit the Cliff Walk. 

If you walk the full 3.5 miles you will probably be ready for dinner and some drinks. If you want to eat dinner at a reasonable time, I recommend making reservations. Kevin and I didn’t and had to wait a few hours for a first come, first serve table at 22 Bowen’s. Kevin’s 45 day aged steak was worth the wait! If you made a reservation and have some time to spare, take a walk up and down the piers of Bowen’s Wharf. 

Instead of coming back into Newport for breakfast the next morning, we stopped at the Black Goose Cafe on our way to Providence.

Providence, Rhode Island

Kevin and I didn’t spend too much time in Providence because a lot of the places we were trying to go were closed, probably due to the fact that we visited during Brown’s graduation day. The streets were lined with cars and full of pedestrians. We found a spot to park near Wickenden Pub and spent some time walking up and down Wickenden Street. The pub and The Duck & Bunny, “a snuggery”, were closed but we found Amy’s Place and stopped in for a smoothie. Wickenden St. is also known for its record stores and Kevin has quite the record collection. He was very excited to load my luggage down with classic record purchases, like he has on previous trips, unfortunately, most of the record stores were closed. We did have the opportunity to stop into Olympic Records however, located just around the corner from PVDonuts, Rhode Island’s First Specialty Donut Shop. PVDonuts like most other specialty donut shops, had a line out the door and up the street. 

After Wickenden St, we had planned to check out Brown, take in the view at Prospect Terrace, walk a mile through history on Benefit St, grab some food on Historic Federal Hill, and perhaps take a boat tour at Waterplace Park. Alternatively, with the crowds, we thought it would be better to get back on the road and head to Mystic, CT. 

Mystic, Connecticut

Naturally, our first stop in Mystic was at Mystic Pizza, the nostalgic spot that inspired the 1988 film, for lunch. After a slice of your typical frozen pizza, we took a stroll through the Olde Mistick Village and hopped in and out some of the cute shops on the main street. We toyed with the idea of stopping in at the Treehouse at the Oyster Club or the Barley Head Brewery at the seaport, but decided to continue on. 

If visiting in the Fall or Winter (September – December) you may also chose to visit B.F. Clyde’s Cider Mill for some fresh cider, hard cider or apple wine. They also have cider making demonstrations. 

If you passed on Treehouse and Barley head like us, but instantly regret it, don’t worry Outer Light Brewing Company is only 10 minutes away and on the way to New Haven.

New Haven and Haddam, Connecticut

While I am sure that Connecticut has its draws, Kevin and I struggled to find anything touristy to do. I enjoy visiting different campus’ so a stop at Yale University was a must; but other than that and grabbing a burger at Louis Lunch, birthplace of the hamburger, we didn’t have much else planned.  To our disappointment Louis Lunch is closed on Sundays and Mondays and therefore, we didn’t even get to try it. 

With not much more to do in Connecticut, Kevin saved the day!  When planning trips, Kevin is very go with the flow. He will take a peek at my itineraries, do a little bit of research himself and tell me his must see and dos. Having done some prior research, Kevin had found that his eighth great grandfather had actually founded Haddam, Connecticut. Not only that but both his seventh and eighth great grandfathers were buried in Haddam.

When in Connecticut, you visit your ancestors, and just like that we started our adventure to The Old Burial Yard of Thirty Mile Island Plantation, established in 1667, in Haddam, CT! 

We spent about 30 minutes roaming the cemetery and found many gravestones that were perceived to be in some way related to Kevin. After some further comparisons to a photo that he had saved on ancestry.com, we were actually able to find his seventh great grandfather, Captain Caleb Cone’s,  worn tombstone. It being Memorial Day weekend, it was touching to see that the town had placed American flags next to the graves of those who had served. For just going out on a whim, our trip to Connecticut will now forever be memorable.

Back to Massachusetts

This being the last stop on our Memorial Weekend Trip, we grabbed dinner at Patriots Place, spent the night at the Boston Park Plaza, and caught a flight out the next morning. 

Stay Tuned for New England Road Trip Part 2 – New Hampshire and Maine!