Iconic lighthouses on magnificent cliffs, fishing villages, mountain resorts, lobster fresh from the boat, history, baseball, and breweries summed up our honeymoon through New England.
We planned this trip beginning in NYC, then going up the coast of New England, and then down the middle ending back in upstate NY which would allow us to cross off NY, MA, RI, NH, ME, and VT from our #50StatesChallenge. It was ambitious but so much fun. It was also a lot of car time – so a good travel companion is key. Audiobooks are also helpful!
Maine is a beautiful place that I paradoxically want to hoard to myself and share with everyone I meet.
John Hodgman
We got engaged on Broadway in NYC so it was fitting that we started out our honeymoon there to see Hamilton The Musical. I have no words for how amazing this show is. Our stay in NYC was brief so that we could be on the way to CT in search of the best pizza in the U.S. and then a tour of the Gilded Age mansions of RI.
We spent two days in Boston, a world-class city with a small-town feel and a hub of culture, history, architecture, and food. The Freedom Trail and a Red Sox game were on the bucket list. So was Salem, MA which was our next destination.
We spent some time in the coastal towns of Portsmouth, NH; Kennebunkport, ME; and Portland, ME in search of the lighthouses, good food, whoopie pies, and the best lobster rolls. We made a detour to Bangor, ME just to see Stephen King’s gothic victorian home.
Our final destination was the Baseball Hall of Fame in Cooperstown, NY. It was a whirlwind 8-day trip and I wouldn’t change a thing.
8-Day Itinerary Without Kids
| Day | To | From | Mode | Departure Time | Arrival Time | Trip Notes |
|---|---|---|---|---|---|---|
| 1 Sat. | Scallywags Irish Pub & Restaurant (Hell’s Kitchen) NYC | FredCo, MD | Car | 12:30PM | 5:00PM | We left the day after our wedding and our first dinner was in the Hell’s Kitchen area of NYC which has amazing dining choices. |
| Hamilton The Musical Richard Rodgers Theatre, Broadway, NYC | Hell’s Kitchen | Walk | 6:15PM | 6:30PM | A must-do at some point in your life, even if you’re not a fan of musicals! | |
| EVEN Hotel Norwalk, CT | Broadway, NYC | Car | 10:00PM | 11:30PM | This is branded as a “wellness” hotel with exercise equipment in the room. Neat concept but we didn’t use any of it. | |
| 2 Sun. | Breakfast at Sono Harbor Deli & Cafe, Norwalk, CT | EVEN Hotel | Car | 8:00AM | 8:10AM | Norwalk’s downtown area is charming – a cute little coastal town |
| Pez Factory Visitor’s Center, Orange, CT | Sono Harbor | Car | 9:00AM | 9:50AM | A fun stop to add to the trip, with or without kids! | |
| Frank Pepe Napoletana Pizzeria, New Haven, CT | Pez Factory | Car | 11:30AM | 11:00AM | A must-stop! Frank Pepe’s is one of the oldest and most well-known pizzerias in the U.S. | |
| Yale University, West Haven, CT | Frank Pepe’s | Car | 10:30AM | 11:00AM | This was a quick stop and photo opportunity. | |
| Cliff Walk, Newport, RI | Yale | Car | 11:15AM | 1:00PM | A must-do 3.5-mile ocean view walking tour of Newport’s cliffs and Gilded Age mansions. | |
| Breaker’s Mansion Tour, Newport, RI | Cliff Walk | Walk | 2:00PM | 2:15PM | The Breakers is the grandest of Newport’s summer “cottages” and a symbol of the Vanderbilt family’s social and financial pre-eminence during the Gilded Age. Splurge on the self-guided audio tour. | |
| The Verb Hotel, Boston, MA | Newport, RI | Car | 4:00PM | 6:00PM | A must stay at Boston’s coolest music-themed hotel with patio views of Fenway Park (so close that a ball could easily hit the windows). Each room features an artist. We stayed in the “Queen/Freddie Mercury” room. Note – if you don’t like loud music, this is not the place for you! | |
| Hojoko, inside of The Verb Hotel, Boston, MA | Our Hotel | Walk | 6:30PM | 6:35PM | Great spot for sushi and ramen inside the hotel. | |
| 3 Mon. | Boston Commons, Freedom Trail, Boston, MA | The Verb Hotel | Uber | 8:00AM | 2:00PM | A must-do and a great way to see the city on foot! We started in Boston Commons and stopped at Faneuil Hall, took a tour of the Paul Revere House, found the Cheers restaurant for a photo op, and stopped at great places like Modern Pastry. The whole trail is 2.5 miles long. |
| Warren Tavern, Boston, ME | Freedom Trail | Do not miss one of the oldest taverns in MA and of the oldest taverns in the U.S. | ||||
| The Verb Hotel, Boston | Freedom Trail | Uber | 2:30PM | 3:00PM | It’s important to build in a little bit of rest time! | |
| Red Sox Game. Fenway Park, Boston, MA | Freedom Trail | Walk | 6:00PM | 6:30PM | We hit the food stations around the park for a ballpark-style dinner. | |
| Cheeky Monkey Brewery, Boston, MA | Fenway Park | Walk | 9:30PM | 9:45PM | There’s a Wild Blueberry Beer there that caught my attention. | |
| 4 Tues. | Salem Witch Trials Memorial, Old Burying Point Cemetary, and Salem Witch Village Salem, MA | The Verb, Boston, MA | Car | 7:00AM | 8:00AM | We arrived in Salem early so we had ideal parking close to the Salem Witch Village where everything is within walking distance. A simple, yet dramatic memorial of the 20 victims who died in 1692. |
| House of Seven Gables, Salem, MA | Salem Witch Village | Walk | 9:30AM | 9:45AM | A national historic landmark, the house is best known as the setting of author Nathaniel Hawthorne’s 1851 novel. I didn’t book the tour early but they were able to accommodate us anyway. | |
| Salem Maritime Waterfront National Historic Site, Salem, MA | House of Seven Gables | Walk | 10:00AM | 11:00AM | The first National Historic Site in the US incorporates 600 years of New England’s maritime history. | |
Lunch at Portsmouth Brewery, Portsmouth, NH | Salem, MA | Car | 12:00PM | 12:45PM | A brewpub with a good food menu right on Market St. in the heart of downtown. | |
| Bush Compound Kennebunkport, ME | Portsmouth, ME | Car | 2:00PM | 2:30PM | Driving along the coastal town of Kennebunkport and you’ll surely come across the Bush family summer home. | |
| H.B. Provisions General Store, Kennebunkport, ME | Bush Compound | Car | 2:45PM | 3:00PM | Some say this general store has the best whoopie pies, a Maine favorite, so we had to try them out. | |
| Portland Head Lighthouse, Cape Elizabeth, ME | Kennebunkport, ME | Car | 3:15PM | 4:00PM | Do not miss Maine’s oldest lighthouse. | |
| Courtyard by Marriott, Downtown Waterfront, Portland, ME | Kennebunkport, ME | Car | 4:15PM | 4:30PM | We got a good deal on this hotel and were pleasantly surprised at the harbor view and how well the location worked out. | |
| DiMillo’s on the Water, Portland, ME | Courtyard by Marriott Waterfront | Walk | 6:00PM | 6:15PM | A floating boat restaurant with a harbor view serving all the Maine classics. | |
| Liquid Riot Brewery & Distillery | DiMillo’s | Walk | 8:00PM | 8:15PM | Great spot to enjoy housemade libations in a hip warehouse setting. | |
| 5 Wed | The Holy Donut Portland, ME | Courtyard Marriott Waterfront | Walk | 7:00AM | 7:15AM | A must-do! Unique potato donuts! |
| Steven King’s House Bangor, ME | Portland, ME | Car | 8:00AM | 10:00AM | Bangor was out of the way from our coastal journey but my husband is a big Stephen King fan so this was a must-stop for us. | |
| 31-foot tall Paul Bunyan Bangor, ME | Steven King’s house | Car | 10:15AM | 10:30AM | Just down the street is a quirky statue of Paul Bunyan. When in Rome… | |
| Bed & Breakfast Bar Habor, ME | Bangor, ME | Car | 11:00AM | 2:30PM | The drive from Bangor to Bar Harbor is only about an hour but somewhere along the way, we stopped to get out of the car and play a round of golf. A great way to stretch! | |
| Bar Island, Bar Harbor | Our B&B | Walk | 4:00PM | 4:30PM | It is only during low tide that visitors are able to walk on the gravel sandbar to the small, uninhabited Bar Island that is situated just across from the town of Bar Harbor. | |
| 6 Thurs. | A Great Maine Breakfast, Bar Harbor, ME | Our B&B | Walk | 9:00AM | 9:30AM | A must-stop for unique Maine breakfast choices. |
| Acadia National Park, ME | Downtown Bar Harbor | Car | 11:00AM | 11:15AM | A must-do. Cadillac Mountain is the highest point on the east coast and offers magnificent views of a glaciated coastal and island landscape. It is the first place to view a sunrise in the U.S. from Oct-Mar. | |
| Main Street Downtown shopping, Bar Habor | Acadia NP | Walk | 3:00PM | 3:15PM | Don’t miss Ben and Bills Chocolate Emporium and their lobster-flavored ice cream! | |
| Stewman’s Downtown Lobster Pound, (Mt Desert Island), Bar Harbor | Main Street | Walk | 5:30 | 5:45PM | Great fresh seafood fresh from the boat! | |
| 7 Fri | White Mountains of NH | Bar Harbor | Car | 8:00AM | 1:00PM | Driving across ME back through NH took us through the White Mountains. This was the longest leg of our trip through windy mountains! |
| Ben & Jerry’s Factory Tour Waterbury, VT | White Mountains | Car | 1:00PM | 2:15PM | A must-do when in Vermont. My favorite part was the graveyard of retired Ben & Jerry’s ice cream flavors. | |
| Cabot Cheese Store, Waterbury, VT | Ben & Jerry’s | Car | 4:00PM | 4:10PM | I had to stop in Vermont and sample Vermont cheeses. This farmers’ co-op store has every kind of cheese you can imagine. | |
| The Alchemist Brewery, Stowe, VT | Cabot Cheese Store | Car | 5:00PM | 5:05PM | If I am being honest, my husband wanted to go to VT so that he could visit The Alchemist and get a Heady Topper – one of the best beers in modern history. The brewery only distributes around the area and produces its beer in small batches. | |
| Sun Inn Ski & Suites Stowe, VT | The Alchemist | Car | 6:30PM | 6:45PM | The hotel included a bowling alley on the property and restaurant. It was a great place to relax. | |
| 8 Sat | Baseball Hall of Fame, Cooperstown, NY | Stowe, VT | Car | 7:30AM | 12:30PM | A must-do! This drive was beautiful through the Adirondak Mountains and farmland into a tiny town called Cooperstown. |
| Home | Cooperstown, NY | Car | 5:00PM | 10:30PM |
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