SydneyPaige This 3 day jam packed road trip itinerary covers Connecticut, Rhode Island and Massachusetts. Highlights include exploring the home of Yale University, The Freedom Trail, and coastal mansions along Newport’s cliffs. This three day road trip will give you a taste of Southern New England.
This trip kicks off my travel goal to visit all 50 states before 30. With these three under my belt, I am at 20!
Planning:
My main goal was to see a little bit of all three states, enjoy some good food and spend some time outdoors. We didn’t want this trip to be too big as far as length, budget and even planning. Just a nice little getaway weekend. Each trip or vacation is going to look different. It’s all about your goals and what you want to get out the trip. My boyfriend was especially excited for Boston. So a day and a half was saved for Boston, and the other day and a half was going to be spent in Rhode Island and Connecticut. So we had a jam packed first day planned for Connecticut and Rhode Island.
Although this is a short three day trip it does require some preparation. There was a winter weather advisory and this trip includes a lot of driving. I chose to take my car and made sure to get oil change before the trip. You can also rent a rental car if your car isn’t in the best condition, or if you’d rather not put miles on your own car. While this trip is amazing anytime of year, I have added some winter tips as this area of the country does get some serious snow in the winter.
Budget
Normally, I like to book as many things prior to the trip, but with this trip hotels were really the only part to book prior. But, that doesn’t mean you can’t budget or plan! Transportation and hotels were the bulk of the cost.
- 2 nights at 2 different hotels – $456
- Tolls – $56
- Gas – $82 (2 full tanks but only used 1.5)
- Parking – $110
Day One:
New Haven, Connecticut
Packed up the car with a full tank of gas, left Philadelphia and headed to New Haven, Connecticut. New Haven is a coastal city that is the Home of Yale University. This was about an 3 hour drive. The earlier we woke up the earlier we could hit the road.
First stop, Brunch! Yelp reviews mentioned a wait, so I made sure to keep an eye on the waitlist as we got closer to brunch. The Place 2 Be is right off Broadway which is near tons of shopping. You place your order through their QR code and they bring it right out to you. My boyfriend got the Philly cheesesteak omelette and I got the churro french toast. Both were amazing and you didn’t even need syrup for the french toast it was that good. The drinks were so cute, you can pick your flavor and they came with little rubber ducks.
Newport, Rhode Island
After a delicious and fun brunch we headed to Newport, Rhode Island. This drive was about 1 hour and 45 minutes. We used directions to the Chandler Hotel as it was right next to the access point for the cliff walk. Street parking was available along Easton’s Beach. The cliff walk is free and so is parking if you go from November to April.
The sounds were calming. It’s a 7 miles round trip walk. This was the perfect date for couples, solo or for families. The famous forty steps is less than a mile from the start of the trail.
The terrain of the walk got a bit rougher about halfway through. The portion of the Cliff Walk between Narragansett Avenue and Webster Street is closed and there is a detour. Along the cliff walk you will pass Salve Regina University, you’ll see many public mansions along the way as well.
Providence, Rhode Island
After the cliff walk we headed back to the car to drive to our final destination for the night, Providence Rhode Island. Checked into the Courtyard Providence Downtown, it was $30 to park in their parking lot. It would have been cheaper to find street parking.
DePasquale Square is the center of Federal Hill, surrounded by tons of bars, restaurants and unique little shops. After exploring the area, we headed to the Providence Oyster Bar for some happy hour food. They had many options, we enjoyed the sushi, oysters, wings and burgers.
After dinner, we headed to the Amica Mutual Pavilion in downtown Providence for a concert. We had floor seats but because of the crowd and people standing on chairs I would recommend getting seats in the bottom section. That way you can see over the people on the floor and your view isn’t blocked.
Day Two:
Morning in Providence
After a jam packed first day, we slept in a little enjoyed a free hotel breakfast before packing up and heading to Boston. Weather picked up as the drive went on with snow.
Boston, Massachusetts
The Mozy
After arriving in Boston, we drove around for a bit looking for parking and had no luck so we decided to check into hotel and grab parking info from them. They suggested a garage down the street, which ended up being about $80 for 30 hours or so. After parking the car we checked in at the Moxy, check in was on the second level. The first floor was very cute with a photo booth and vibrant pink signs everywhere.
The rooms were small, it might not be ideal for a long stay but it’s perfect for a weekend if you are traveling solo or as a couple. There is minimal storage space but hooks on the wall. The hotel didn’t advise of the $25 destination fee but from reading reviews before hand I knew it was going to be charged at check in, so just keep that in mind. The hotel does give a $25 resort credit and gave two drink vouchers, so it evens itself out.
Despite the small room, the hotel made up for it in amenities. On the second floor they had a bar/lounge area with drinks, light snacks and games. They had a rooftop bar where in the morning there was an all you can eat brunch and in the evening it turns into a mini night club. With a few gaps in the day such as in between arrival and lunch, the lounge area was perfect for hanging out.
After some drinks, playing games and hanging out at the hotel we walked to lunch. We went to Citrus & Salt for the birria tacos but they didn’t start serving them til dinner. Brunch ended at 3:45pm, restaurant was closed until dinner that started at 5pm. So we got a few appetizers and drinks instead.
We relaxed at the hotel in between brunch and dinner. Less than a half mile walk is this vibrant seafood restaurant – Bootleg Special. I made dinner reservations before hand which was a good idea because they were pretty packed. The portions were large and flavorful. The build a boil was very customizable.
Day Three:
Morning in Boston
Started off the morning with breakfast on the second level and a rooftop drink after. Although, there was an all you can eat buffet style breakfast on the rooftop. Did you know that in Boston, alcohol is illegal before 12pm on Sundays? You learn something new everyday!
Boston Public Garden
We packed up all of our stuff and then loaded up the car and kept it in the garage. The first stop was the Boston Public Garden it reminded me of a mini central park. It would be even more lively in the spring and summer. Boston’s Public Garden was the first public botanical garden in America.
The Boston Commons is directly across the street and the perfect way to start the Freedom Trail. But depending on where you stay and where you want to end the trail you can start anywhere. Some stops along the trail are free and some charge an admission.
The Freedom Trail is a 2 and a half mile walk passing by historic monuments throughout Boston. I used the all trails app to guide me on the trail, you could also pay for a guided tour.
The Freedom Trail Sites
- Boston Common
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- King’s Chapel & King’s Chapel Burying Ground
- Benjamin Franklin Statue
- Old Corner Bookstore
- Old South Meeting House
- Old State House
- Boston Massacre Site
- Faneuil Hall
- Paul Revere House
- Old North Church
- Copp’s Hill Burying Ground
- USS Constitution
- Bunker Hill
There are even more places to check out in between each site, like the Quincy Market and the Boston Public Market. The Freedom Trail is perfect if you only have a certain amount of time in Boston, you can see so much in less than 3 miles.
Some of the sites like Massachusetts State House were closed due to it being the weekend. So keep that in mind when planning your Freedom Trail Itinerary.
Quincy Market is the best place to stop along the Freedom Trail for some food. You have to get a lobster roll at some point in your weekend and this Oyster Bar inside Quincy Market is the place. They sell both hot and cold lobster rolls and comes with a bag of chips.
Inside the Public Market was a cute stand for Red Apple Farm where they sell apple products of all kinds, juice, donuts and cider.
Finishing up the Freedom Trail, we ended at this vivacious brunch; Wicked Craft. Make sure to make a reservation, this place may be small but gets packed fast. They had the best charcuterie I have ever seen at a restaurant! The best part it was only $18. I ordered the “one” person charcuterie but we both enjoyed it. After the brunch, we walked back to the garage where the car was parked and made our journey back to Philadelphia.
