new-england – Trip Trek Go

Come along on a Fantastic Fall Getaway through New England. If you are like me, you love checking off states that you have visited, here is a trip that includes FIVE. We say it only “counts” if you sleep there and this adventure will take you through 5 states in 7 days, and I promise you don’t feel like you are driving too much. We used Enterprise and rented a Jeep Wagoneer for our family of 5 with 4 suitcases and a backpack for each of us and we had plenty of room.

We started our adventure with a direct flight on JetBlue from Los Angeles to Boston. Jet Blue offers free Wi-Fi, complimentary soft drinks, snacks and was a great choice for low fare airlines. Just do not forget your wired headphones if you plan to use the TV on the seat in front of you. Our plane had the MINT seats in the front and those looked amazing! Maybe one day, right JetBlue?

Once we landed, we stayed at the Springhill suites by Marriott on Revere Beach. It comfortably slept all five of us and had a free airport shuttle, as well as complimentary breakfast. The local enterprise picked us up in our Wagoneer the next morning to fill out the paperwork and rent our car. It was around 6 minutes from the hotel and extremely convenient. Once we had our SUV, we hit the road the Salem (with a quick stop in Saugus, because that is where my husband grew up; but the CA version). Salem was about 30 minutes from the Boston area, and we parked in the parking garage right in the middle of town for about $6. During weekends in October, this increases to about $40. This town is known for Halloween, so that makes sense. We walked around, following the yellow and red lines painted on the ground to take you to all of the hot spots. We ate at Dire Wolf which had delicious sushi along with American fare and drinks. We decided to take the hour-long ferry to see all of the sites in the town, including the Bewitched statue, a few Hocus Pocus sites and listen to all the history of the famous Salem Witch Trials. Did you know Salem has its very own Waikiki Beach? This is located on Winter Island and is a gorgeous place to take pictures with a light house in the background.

After spending a few hours in Salem, we continued on for 54 minutes to New Hampshire and stayed at the AC Portsmouth Downtown/Waterfront hotel. There is a rooftop restaurant and bar with igloos during the fall and winter months. Portsmouth is located in New Hampshire (there is also one in Rhode Island that we will drive through later in the trip). Portsmouth is the cutest New England town to walk around, visiting cute bakeries and coffee shops, boutiques and restaurants and right along the waterfront. The one thing we did not do here that I wished we had was the Seal Walk at the Sea Coast Science Center. It started at 11:30 and we were booked to take our family photos in Maine at 3:15, so I didn’t want to risk being late.

After visiting a few shops and enjoying coffee and croissants downtown, we headed up north to Portland Maine, which was just 52 minutes up the road. In Maine, we stayed at the Westin Portland Harborview. These rooms were on the smaller size, only full-size beds, so we opted for two connecting rooms here. It is in the heart of Downtown, walking distance to Otto’s pizza, famous for their Mashed Potato, Bacon and Chive pizza. My favorite was the Hot Honey pizza. After checking in and getting some appetizers and margaritas, we headed to Cape Elizabeth and the oldest lighthouse in Maine. Following our pictures, we headed to Freeport Maine, site of the L.L. Bean Flagship store that is open 24 hours a day. There are various shops and outlets to walk around as well as restaurants to dine in. The next morning, we headed to Kennebunkport, Maine and saw more adorable boutiques, coffee shops, the summer home of President Bush and his family and gorgeous coastal views. Maine may be one of the most beautiful states, I have ever visited.

Next, we headed to Vermont. This was the longest drive on our trip so far and would be a two-hour drive. The gorgeous, wooded area and a few trees still hanging onto the last of their gorgeous fall leaves, made it go by quickly. We pulled into Brattleboro and the kids enjoyed swimming and a fire pit, while my husband and I enjoyed Vermont Cheese, breadsticks and wine we grabbed at the grocery store. In Vermont, we visited The Retreat, which has beautiful hiking trails, animals and an adorable store/gift shop. You can’t miss the Vermont Country Deli, where we had sandwiches, treats for the drive and just up the road from a gorgeous, covered bridge. These were called the kissing bridges when they originated because of the privacy they offered. The most unique hotel in Brattleboro is called the Viking Villages. These are small viking style cabins that are perfect for families and about 15-20 minutes from town. We were originally going to stay there, but the kids wanted to be somewhere with a pool, and these were more secluded. From Vermont, we headed back to Massachusetts, with a stop at the battlefield of Concord and Lexington. Our son is in fifth grade and his teacher told us they would be learning about the minute men and that battle, so we made sure to stop by so he could see it.

We could not stay too long, as we had 3:00 tickets for the Fenway Park Tour. We headed straight there and lucked out finding street parking next to the stadium. We toured Fenway and were able to sit in the Green Monstah seats. We went into the Press Box and heard all about the history. This was one of the most fun games to see, because of the seventh inning stretch that included signing “Sweet Caroline”. The history at this ball park is amazing and we were lucky enough to catch a game here in 2019. After the tour, we were parked right in front of the Yard House and we were all starving, so we stopped in for their Happy Hour. Their happy hour is only for food and included their pizzas. I loved the $8 poke nachos that I ordered. After our late lunch/early dinner, we drove to our hotel, Boston Marriott Long Wharf. We used points and one of our upgrades to stay in a one-bedroom suite. This hotel is right on the water, walking distance to Quincy Market and Faneuil Hall, the aquarium and is stop 1 on the hop on, hop off tours. Here we walked some of the Freedom Trail, visited Paul Revere’s house and enjoyed the views of the harbor. That night we stopped into Faneuil Hall for ice cream and clam chowder. The next morning, we rode the 2-hour full loop of the hop on, hop off bus to hear the history and see the city before we headed to Rhode Island.

We drove to Rhode Island, about 90 minutes from Boston and stayed at the Newport Hotel and Spa. It was walking distance to all kinds of shops, restaurants, has gorgeous views of the harbor and was another great Marriott property. While in Newport, we visited the mansions, The Breakers and walked a portion of the Cliff Walk.

We flew home out of Providence the day before Thanksgiving, and it was wonderful. No lines, no crowds, an open middle seat, and it was only 30 minutes from Newport (via the toll roads). We were even interviewed by their local news team (Channel 12 WPRI) for braving the holiday travel the day before thanksgiving.

We flew home on Southwest and I continued my streak of earning a free glass of wine for locating Chick Norris in the emergency pamphlet.

Lets jet set off to Boston from Los Angeles. First things first, we have to book our flights. You know me and my love of a good deal, and we found exactly that on Frontier https://www.flyfrontier.com/ . We chose Frontier due to their promotion of KIDS FLY FREE (up to 16 years) on some roundtrip flights (if you are a part of the Discount Den, $59.99/annually). This promotion worked perfect for our situation, as we were gifting this trip to my mom as a retirement present, so we had three adults and three kids flying and only paid for three round trip tickets. As a note for Frontier, you can find some amazing deals. I once flew from Los Angeles to Denver for $7.00!

So, back to the trip… Our flights had us arriving relatively late, so we stayed near the airport prior to heading to Chatham the next day. For hotels near the airport I recommend Courtyard Boston Logan Airport https://www.marriott.com/en-us/hotels/bosla-courtyard-boston-logan-airport/rooms/ if you are using points or The Westin Boston Seaport District https://www.marriott.com/en-us/hotels/bosow-the-westin-boston-seaport-district/overview/ for a good rate and I love how Westin hotels smell.

On the drive to Chatham, we stopped at Pilgrim Memorial State Park for some slushies and to get a first hand look at Plymouth Rock. It is an actual rock you can view. It does have a fence around it so you are not able to touch it. Plymouth Rock is located next to a gorgeous harbor with boats and a river running near the town in the Brewster Gardens area. If we had more time, I think this adorable spot would be a wonderful place to spend the day.

We arrived to our Airbnb http://www.airbnb.com at grabbed some coffee at Monomoy Coffee Company, which is now called Chatham Perk https://www.chathamperk.com/ The entire downtown area is adorable in Chatham and had some cute shops and restaurants.

The next day we walked around fabulous homes in South Chatham and played “if we won the lottery…” and visited a beach with a library style shovel and bucket wall to share. The beaches have “Be Shark Smart” signs all over, which was a bit intimidating, but the water was amazing and we felt safe, even in the water close to the shore.

After our morning at the We ate lunch at Sandi’s Diner, where the motto is “Sandi’s Diner, Nothing is Finer”…however it too has now been sold and it now called Lily’s diner https://lilysdiner.wordpress.com/everday-menu/

After lunch we walked down to the beach near the U.S. Coast Guard Chatham. We found a spot at Chatham Lighthouse Beach and relaxed for the afternoon, building sandcastles, playing in the water and taking pictures with the lifeguards. Being from the west coast, the east coast ocean always feels so warm and refreshing.

That evening we went to Chatham Bars Inn https://www.chathambarsinn.com/ for Happy Hour and to take in the view. This is an absolute must see and was gorgeous! We sat in adirondack chairs, on a hill overlooking the ocean and then ended the day with ice cream and grabbed the http://vineyardferries.com map to plan the rest of our adventures. We would be leaving from Woods Hole, MA to Martha’s Vineyard, with a stop in Hyannis Port along the way.

The next afternoon we drove to Hyannis Port. I have a slight obsession with the Kennedy Family and wanted to see the Kennedy Compound. We were able to drive to the block on Marchant Avenue where the homes are located. Three homes make up the Kennedy compound and Ethel Kennedy still lives in 20 Marchant Avenue; however the “big house” located at 50 Marchant Avenue was donated to the Edward M. Kennedy Institute for the US Senate in 2013.

In Hyannis Port, we found shells, walked on the beach and headed to Woods Hole to catch the ferry. The ferry was an easy trip to Oak Bluffs where we sat on the top level to breathe in the ocean air and feel the wind in our hair as we made our way to Martha’s Vineyard. Once we arrived, we ate lunch at Fishbones Bar and Grille https://fishbones-mv.com/, walked around Edgartown, of course had to visit Lily Pulitzer and Vineyard Vines and made our way back to South Boston after our day trip. I have visited Martha’s Vineyard twice on day trips and would love to stay the night next time. My recommendation is for the Harbor View Hotel & Resort and Kelley House in Edgartown https://harborviewhotel.com/ I worked with the previous general manager at this resort and was able to visit and enjoy some wine and lobster rolls on the wrap around porch and would love to come back to stay. The resort was stunning and the food and beverage experience was first class. I can just imagine the rooms and service would be just as pristine.

Once back in the city, our Airbnb was on Atlantic Street in the Boston neighborhood of Dorchester Heights. We were able to walk over to the location of the American Redoubts from our home, which compelled the evacuation of Boston by the British army. The area is close to public transportation and worked well for our large group. We also walked through Thomas Park and onto Carson Beach from our house, which is perfect if you have young kids that love the sand.

While in Boston we visited the Paul Revere House, walked along the Freedom Trail, caught a Red Sox game at Fenway Park, where the kids were able to run the bases and we all joined in singing “Sweet Caroline” for the seventh inning stretch. At Fenway, there is a bar (Bleacher Bar https://www.bleacherbarboston.com/ )that opens up to the field before and after the game that was fun to visit.

One of my favorite things to do in places with a lot of history in the hop on/hop off tour bus. We took it all over Boston, to MIT, Cambridge, walked around Harvard and had lunch at Cheers https://www.cheersboston.com/; which is also a family friendly restaurant. We visited the location of the Boston Tea Party, ate lobster rolls and found a rooftop bar on the water to have some drinks to complete our trip. This is my son on the steps of Harvard, on what should have been his first day of Kindergarten. Flights were best the next day and he is our third kid, so his “first day” of Kindergarten was everyone else’s second day. Life of a third child-ha! I absolutely recommend this area for a family vacation, couples trip or even to explore solo. It is a gorgeous part of the US filled with history and beauty. Safe Travels!