A Week in New England

If you have a week in New England to do a road trip, then this blog post is for you! We started out with nothing but a list of sights to see. We didn’t reserve anything ahead. This was our experience…

Burlington Stowe, and Barre, Vermont

Church Street Marketplace is a great first stop to enjoy some trendy shops and restaurants on Burlington’s main pedestrian street. Vermont is known for its farm-to-table eateries and this location doesn’t disappoint! Some amazing dining experiences even overlook Lake Champlain.  Later, we headed over to the Ben and Jerry’s Factory in Waterbury for some delicious ice cream! Check out their Flavor Graveyard!  Cold Hollow Cider Mill is also nearby and is a good place to pick up some famous Vermont syrup, tasty cider donuts, and apple cider. There is even a little section that shows how the cider is made with free tasting cups. 

From here we visited Stowe, a little taste of Austria, with the scenic Stowe Recreation Walk/Bike Path and lots of bike rental places around. There are also opportunities for ziplining or skiing depending on the time of year. Google for coupons or discounts before you go! For great views take the Stowe Mountain Auto Toll Road up to the top of Mount Mansfield (also a 10-minute optional hike at the top). There are a lot of great dining options in Stowe as well! 

Next, we headed south towards Barre (pronounced Berry) where you will find all things granite. You can visit the Rock of Ages Quarry and drive around the Hope Cemetery to locate some elaborate granite headstones. Stay at the Maplecroft Bed and Breakfast for a real Vermont experience with a wonderful breakfast and friendly host! 

Massachusetts/The Berkshires

Continuing south, we headed towards Mass MoCA in North Adams, Massachusetts for some spectacular modern art. After getting immersed in that land of illusion we headed up to the summit of Mount Greylock to get some fresh air and magnificent views. Be sure to climb to the top of the Veterans Memorial. If you prefer more traditional art, the renowned Clark Art Institute is nearby. For lunch, head to Once Upon a Table or Main Street Cafe in the quaint downtown village of Stockbridge. For more history, we stopped at the Hancock Shaker Village where you can learn how to do the Shaker dance. There are also optional hiking trails across the street that are owned by the village.

Finally, don’t miss the Norman Rockwell Museum to relive some great memories! For more hiking trails and amazing views, check out Monument Mountain. These trails were a popular destination for poets, painters, and novelists such as Nathaniel Hawthorne and Herman Melville. Herman Melville’s Arrowhead home can also be toured nearby.

The Berkshire Botanical Garden, the Mount, the former home of Edith Wharton, and Naumkeag, a public garden and historic home, are also popular destinations in this area. If you are lucky you can catch a show at Tanglewood, the Boston Symphony’s summer home. 

Portsmouth, New Hampshire (Optional Boston, Concord, Salem, Plymouth detour)

Continuing on our week in New England road trip, there is a three-hour drive to our next destination in New Hampshire. Find a hotel along the route as your time permits.  If you have an extra 4 or 5 days, you can detour over to Boston and the surrounding areas. If not, continue onto New Hampshire with us. 

We opted to drive through Newington towards Portsmouth where we passed a cool old neighborhood with a parsonage, stone schoolhouse, Langdon library, old town hall, 1713 meetinghouse,  and an old village forest. In the charming village of Portsmouth, we visited the USS Albacore, the Strawbery Banke Museum (an open-air village museum with authentic 17th and 19th-century buildings), the Wentworth Gardner House and the nearby 17th century Point of Graves Burial Ground. If you have more time, please visit the  John Paul Jones Museum (includes entrance to the Portsmouth Welcome Center with a great historical short film of the area). Another great spot to visit along the New Hampshire coast is the Hampton Beach and the boardwalk. 

York, Ogunquit, and Kennebunkport, Maine

A week in New England road trip is not complete without a visit to Maine, where we will begin to drive up the coast. Be sure to stop by the seaside towns of York, Ogunquit, and Kennebunkport. Here are the places we loved along the way…


Old York Historical Society– southern Maine’s largest collection of historic properties. We had time to just visit the Remick Gallery and the old Gaol, but they have lots of other old museum sites if you have time. 

Cliff Walk York: Not to be missed easy trail along the coast with gorgeous views of cliffs, the beach, and some amazing homes! 

Nubble Light: Passing long stretches of beautiful beaches, we were so excited to see our first iconic New England lighthouse! Not only is the view amazing, but the lighthouse is right next door to the popular Fox’s Lobster House where you can enjoy some of Maine’s freshest seafood. You will see Fox’s Lobster House chips sold throughout Maine. We loved these! 


On our way to Perkins Cove, a picturesque harbor filled with art, crafts, restaurants, and scenic views, we came upon the gorgeous Ogunquit Museum of American Art. From Perkins Cove you can take a scenic walk along the Marginal Way; a mile and a half paved path along the water’s edge. If you don’t want to walk back, Ogunquit’s trolleys can drive you back to Perkins Cove.  


Next, we drove through Kennebunkport Historic District, another great stop for shopping and dining, on our way to Blowing Cave Park (Parson’s Way), in hopes of seeing the water shoot up. We didn’t find luck there, but we did discover across the way, Walker’s Point, the George Bush Family Compound. We tried to get closer to check it out but were stopped by the Secret Service. Don’t try that! 

Old Orchard Beach, Portland, Freeport, Owls Head, Rockland

Old Orchard Beach is a beautiful, expansive light sand beach with a fun pier, and an Amusement Park/ Arcade (check hours) called Palace Playland. We had a lot of fun walking up the pier, checking out the views, the shops and the eateries, Click here to see all of the things to do in this area. Continuing up the coast we pulled into Fort Williams Park to explore the old mansion and military ruins and see the Portland Head Light, the oldest and most photographed lighthouse in America.

Portland has a lot to offer including museums, art galleries, restaurants, and its Old Port. The historic center displays cobblestone streets and brick buildings from a time gone past. Areas of attraction include the Portland Museum of Art, Maine Historical Society, and the Portland Waterfront Historic District. We opted to visit the International Cryptozoology Museum (must pay to park here), because we are weird like that! 

Freeport, Maine is the land of L.L.Bean and was our next destination. Of course, we had to photograph the giant boot, the bootmobile, and do a little shopping! We then had dinner at the fabulous Tuscan BistroHere are other things to do in Freeport. 

While it was growing dark we headed over to Owls Head Lighthouse. We climbed to the top for a view, but there were beautiful surroundings everywhere. 

By the time we arrived in Rockland, it was pretty dark, so we briefly visited the Rockland Breakwater Lighthouse and stayed the night in town. We had planned for a longer stay here, but being short on time, we decided to head to our final destination, and the highlight of our trip, Acadia National Park.

Acadia National Park, Bar Harbor on Maine’s Mount Desert Island

The final day of our week in New England road trip is dedicated to all things nature. Hiking was first on our list in Acadia National Park ($30 per car, dog-friendly), so we headed to the Jordan Pond Path trailhead on Park Loop Road; however, being such a popular trail, there was no parking to be found. There also wasn’t any parking for the trail up Cadillac Mountain (highest point on the United States East Coast). In fact, we found that we needed reservations to even drive up to the top of that mountain.

This did not deter us; however, Acadia National Park is huge and there would be hiking trails to be found! To whet our appetites there are overlooks along the way such as Bubble Rock Overlook and  Eagle Lake Overlook. Finally, we found parking near the Stratheden path (easy) which connects to the trail to Dorr Mountain (strenuous) with an amazing view from the top! You can continue on from here to Cadillac Mountain, but that is only for the extremely fit. Here are some other trails you can try.

After returning from this trail we headed towards the beach. A great path from here is the Great Head trail which leads from the sandy beach to the cliffs. Along the Ocean Path Trail, there are great beach overlooks and the famous Thunder Hole where waves crash with a “thunderous boom and high-flying foam” when tides are up. 

At the end of our day, we drove into Bar Harbor and stopped for some lobster of course! We also tried Maine’s official state treat, the Whoopie Pie. My husband was not a fan, but I liked it! There are several mom & pop lobster and crab places around and they are all super fresh!

I hope you have enjoyed A Week in New England Road trip!  Have a great time!

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