Journey through New England

In the fall of 2019 we took a week to journey through several New England states to take in the best of the fall colors, historic sites and cities, covered bridges, lighthouses, and more. Starting and finishing in Rhode Island, we journeyed through Massachusetts, Maine, New Hampshire, and Vermont.

  • Highlights
    • Iron Works Restaurant, Providence, RI
    • Freedom Trail, Boston, MA
    • House of the Seven Gables, Salem, MA
    • Portland Head Lamp, Portland, ME
    • Swift River Bridge, Conway, NH
    • Crawford Notch State Park, NH
    • Apple Picking, Vermont
    • Billing’s Farm and Museum, Woodstock, VT
    • Minute Man National Historic Park, MA
    • Fort Adams State Park, RI
  1. Day 1: Rhode Island to Massachusetts
  2. Day 2: Boston and The Freedom Trail
  3. Day 3: Salem, Portsmouth, and Portland
  4. Day 4: New Hampshire and into Vermont
  5. Day 5: Apple Picking in Vermont
  6. Day 6: Northern Vermont
  7. Day 7: A Long, Slow Drive Back to Rhode Island
  8. Day 8: Newport and Fort Adams

Day 1: Rhode Island to Massachusetts

We flew into Providence, Rhode Island and after getting our rental car, an underpowered Dodge SUV, we stopped off at a restaurant near the airport for dinner. We planned to drive to Massachusetts that afternoon and would return to see more of Rhode Island on our last day.

Restaurants: Iron Works, Providence, RI: 5 Stars
The first meal of the trip was already a home run. We had a calamari appetizer followed by a schnitzel dinner and it was great. Along with the beers this was one of the best restaurants on the trip.

After eating we set off for Massachusetts. Our schedule had us in Boston the following morning so we would be staying in the outskirts of the Boston area. It was a relatively easy 70 mile drive north to Bedford, MA where we checked into our hotel.

Lodging: Doubletree Hotel, Bedford, MA: 4 Stars
This hotel was quite nice for the two nights we would be there and a much more reasonably priced option than the very expensive options in Boston. We payed for the included breakfast which was very good. The only downfall was the size of the beds. A queen sized bed comfortably fits two people. A full size bed does not. Though listed as queen sized, we were sleeping on cramped full size beds.

Day 2: Boston and The Freedom Trail

I had wanted to go to Boston for quite a while before actually getting there with the family. I knew the locations on the Freedom Trail were ordered with what I considered the ‘higher priority’ sites at the end than at the beginning, so we traveled the trail in reverse (if there really is a reverse). When you are walking a 2.5 mile urban trail (5 miles roundtrip) with kids you have to expect that at some point the youngsters will get tired and you don’t want that to happen before you see the USS Constitution and the Old North Church.

Attractions: USS Constitution and Museum: 4.5 Stars

I built a model of Old Ironsides as a kid and couldn’t wait to set foot on the ship. But access to the ship was closed that day. We did go to the USS Constitution Museum which is very good and worth at least a half hour of your time. There are lots of good exhibits which explain everything from the history of the ship in the War of !812 to its construction.

Proceeding down the trail took us across a bridge and to the Copp’s Hill Cemetery.

Attractions: Copp’s Hill Cemetery: 4 Stars


Unless you are in a hurry it’s better to really try to hit every stop on the trail, including the cemeteries. You are journeying back to the Boston of the Puritanical 1600s and the world was cold, scary, and superstitious. Read the gravestones and enjoy the ghoulish engravings.

Attractions: Old North Church: 5 Stars

The Old North Church is too important to the history of revolutionary America to not see. Along with the church there is a demonstration of chocolate making, which is interesting since you don’t normally associate chocolate with colonial America, but apparently there was an important chocolate trade in Boston.

Attractions: Paul Revere House: 4 Stars

No individual is more associated with the independence movement in revolutionary Boston than Paul Revere. His house is an interesting look at 17th century architecture.

After touring the Paul Revere house we fond ourselves in an Italian district with a number of eateries. We were pretty hungry and decided to stop in one for lunch.

Restaurants: La Familia Spagnuolo: 4 Stars

It’s funny to me to read the reviews of this restaurant. Either it’s great or it’s rude. For me it’s the former. Fresh pasta, meatballs, bread, etc make for a great meal along the Freedom Trail. The staff aren’t really rude. It’s just a brusque personality that you either understand or you don’t.

Leaving the restaurant mother nature decided we needed a little rain. With each stop it picked up until later it was a full noreaster.

Attractions: Faneuil Hall: 3.5 Stars
I’ve never been 100% sure how to say Faneuil but I believe it’s “Funeeul”. Anyway, the top level is a large restored hall with a presentation by park service staff, and the bottom level is a large marketplace to buy souvenirs (we bought some). I felt the presentation was a bit too influenced by progressive politics and kind of tainted what could have been a good opportunity to understand how important Faneuil Hall was to colonial Boston.

The rain was really coming down as we left the hall. We still kept going to the next stop, the Boston Massacre Site.

Attractions: Boston Massacre Site: 4 Stars
It’s just a marker but just remember that in the tinderbox that was revolutionary Boston it was this spot that really pushed things over the edge. Without the patriots of Boston agitating against Britain the war might never have even started. Extra points if you can name anyone killed at the Boston Massacre other than Crispus Attucks. I can’t.

Attractions: The Old Statehouse: 4.5 Stars

The Old Statehouse

The Old Statehouse was the center of colonial Boston’s government and just steps from the site of the Boston Massacre. For us this was the last stop before giving up on continuing due to the weather.

A tip for those who don’t want to walk back to their starting place on the trail. Use Uber or Lyft and to go back to your car. For us it was a necessity due to the weather but even if we hadn’t experienced bad weather we probably would have used a rider service anyway.

My plan had been to stay pretty much the whole day in Boston and eat in one of the historic restaurants near the trail. But with the weather we ended up driving back to our hotel before deciding on dinner. I kind of wished we had taken the chance to go back to the city later for dinner.

Day 3: Salem, Portsmouth, and Portland

We started the day early after breakfast at the hotel (which was quite good) and headed off to Salem. One thing about my trip plans is that I try hard to get in as much as I can but often we have to cut things alog the way if the schedule no longer permits it.
There are three big attractions in Salem: 1) The Witch Museum 2) The House of the Seven Gables 3) The Maritime Museum. Since it was October the line to enter the Witch Museum was excessive and we decided to pass on it. Instead we drove over to the House of the Seven Gables.

Attractions: House of the Seven Gables: 4.5 Stars

If you haven’t read the Nathaniel Hawthorne book, don’t worry you can read it after the tour (I did). You will learn a great deal about Nathaniel Hawthorne and his life at the house and see a fascinating 17th century house as well with its unique construction. My kids learned a great deal about Hawthorne between this stop and the Old Manse which I’ll discuss later. I doubt they remember any of it.

We decided to continue north after the house tour and ended up stopping at the Newburyport Custom House and Maritime Museum.

Attractions: Custom House and Maritime Museum, Newburyport, MA: 3 Stars

Evan at the Newburyport Custom House

There are some very interesting exhibits at the Custom House. The presentation isn’t the best. The feel of the building is very cold and dark and honestly a little depressing. But don’t let that deter you.

We were ready for lunch and were determined to improve upon the disappointing meal we had the night before. Portsmouth, NH was our next destination and seemed the ideal place.

Portsmouth is a very historic city. In fact it is one of the oldest in America. From the minute we set foot in the historic center we we kind of awed by the colonial architecture that dates back centuries.

We found the right place to have lunch and waited to be seated.

Restaurants: Portsmouth Brewery, Portsmouth, HN: 3.5 Stars

So absolutely we had chowder, but this time it was good. The restaurant is inside a cool, historic building and it’s neat to just look around the interior. That said, despite getting the beer and chowder we sought it was only a mediocre meal.

At this point we had two objectives for the rest of the day. Lighthouse hunting and finding a lobster dinner. In that order.

Outside Portsmouth we found a couple lighthouses to photograph, then continued north into Main where the fall colors were really beginning to make their gorgeous mark on the trip. We wound around a couple areas where there was a lighthouse but no public property and then struck lighthouse gold.

Attractions: Portland Head Lamp, Portland, ME: 5 Stars

The Portland Head Lamp isn’t just a magnificent lighthouse, the surrounding coastline is incredible. There is also a more distant lighthouse visible to the north and Fort Williams park battery is interesting as well.

As the hours of the day were waning we pulled into our motel for the night in Portland, Maine before deciding on dinner.

Lodging: Fairfield Inn, Portland, ME: 3 Stars
This was a very standard motel, honestly. Certainly it was clean and adequate for the night, but I also don’t think I would choose it over other options in downtown Portland.

Once we were checked in, we looked for a seafood restaurant to have lobster (since we were in Maine). It was not located in Downtown Portland, where I really wanted to be.

Restaurants: Becky’s Diner, Portland, ME: 3 Stars

The lobster is served up fresh off the boat at Becky’s. If you like lobster and no frills or atmosphere, this is the place. Truthfully I’m not a big fan of lobster but I’ll have it in the right places. Would I make this my choice next time, honestly no. I really do like a bit more atmosphere.

Day 4: New Hampshire and into Vermont

Our trip into Maine was always going to be brief, but we also know that we’ll be back to see more of the beautiful northeastern state in the coming years. Still I wish we could have seen more if the timeline permitted.

We left early and started westward through beautiful forests in the height of fall colors.

A reflective lake in western Maine

As we entered New Hampshire near Conway our priority switched to covered bridges. New Hampshire is famous for having them all across the state and our first was the beautiful Swift River Bridge.

Attractions: Swift River Bridge, Conway, NH: 4.5 Stars

Proceeding north we hit the Honeymoon covered bridge as well

Attractions: Honeymoon Bridge, Jackson, NH: 4 Stars

Before entering Crawford Notch State Park to enjoy the incredible fall scenery and to do some hiking.

Attractions: Crawford Notch State Park, NH: 5 Stars

They may be called the White Mountains (and in winter I’m sure they are), but in October they are as colorful a place as you’ll ever see. The hillsides were every color from deep purples, to brilliant reds, to vibrant yellows and oranges. The hike to Ripley Falls was especially rewarding. The forest floor was a carpet of leaves the entire way.

The trip through New Hampshire was going great and our afternoon lunch/dinner in Littleton didn’t disappoint either.

Restaurants: Littleton Freehouse Taproom and Brewery, Littleton, NH: 4.5 Stars

This was my favorite brewpub on the trip and the food was great too. I have to say in many ways New Hampshire was my favorite state on the journey, even if we never slept there.

Finally as evening was coming on we made our way into Vermont and to our hotel in White River Junction.

Lodging: Holiday Inn Express, White River Junction, VT: 4 Stars
The rooms here are perfect for families. We had a two room suite with two televisions and a kitchen area. We were able to order in to save money on dining out as well. My only complaint was the breakfast which was among the worst I’ve ever had at a motel. There was really nothing good to eat and we instead opted for the Dunkin Donuts nearby more than once.

Day 5: Apple Picking in Vermont

Day 5 was an unusual day for us. We slowed down a bit to enjoy the Vermont countryside and for apple picking and to see historic Grafton and Brattleboro.

Attraction: Apple Orchards, VT: 5 Stars

We went to Scott Farm Orchard, which I recommend, but there are dozens of orchards in southern Vermont to choose from. This was a fun activity that resulted in us collecting a couple bags worth of apples to check into our luggage for the flight home 🙂

After bagging all the apples we could ever want we were ready for lunch and drove south to the riverfront town of Brattleboro.

Restaurants: Whetstone Station, Brattleboro, VT: 3 Stars


For views alone this is a 5 star restaurant. If the food could match it (and it wasn’t so crowded by people wanting to get seated) it would be. Unfortunately the food and the grouchy people inside kind of tainted what might otherwise have been terrific.

Attractions: Historic Grafton, VT: 3.5 Stars

After lunch we made our way back north and stopped off in the historic town of Grafton. Grafton looks much as it did at the turn of the 19th century. We went through a small historical museum but otherwise didn’t find much to do in the town other than to enjoy the architecture.

Finally we traveled back to the hotel for the night and called it a day.

Day 6: Northern Vermont

Our last day in Vermont would travel across the state in a northwesterly direction. Our first stop was a combination of history and nature in Smuggler’s Notch.

Attractions: Smuggler’s Notch State Park, VT: 4 Stars

The drive up to the notch was on a windy paved road that taxed the weak engine of the SUV we rented, but when we did arrive we were met by crisp air and beautiful cliff and forest views. We hiked up a trail to the notch and took our photo in the small cave.
The Smuggler’s Notch got its name for being a mountain pass that allowed goods to be smuggled between the United States and Montreal at a time when an embargo blocked trade necessary for Vermont. Thus, goods were smuggled through the pass illegally.

After stopping briefly in Stowe for souvenirs we proceeded on to a necessary ice cream stop.

Attractions: Ben & Jerry’s, Waterbury Village, VT: 3.5 Stars

The ice cream is the reason to go here, along with the humorous ice cream graveyard. Most people are pretty well aware by now that the founders of B&J are progressive liberals and unfortunately they do inject a bit of their politics into the short factory tour. If you can ignore that part it’s a pretty good stop. My youngest, Evan, actually just likes regular vanilla ice cream, and happily calls himself the vanilla boy. The rest of us tried a variety of flavors.

Attractions: Billing’s Farm and Museum, Woodstock, VT: 4.5 Stars

I grew up in an extended family with farmers, but unfortunately my kids aren’t old enough to remember visits to the farm. This was a great way for the kids to experience historic New England farm life and to watch cow milking and more. My kids really liked the newborn calf. We also toured the house for a butter making demo, but don’t be fooled into thinking they’ll give you any for free. The grumpy butter woman was the only negative about the experience.

Day 7: A Long, Slow Drive Back to Rhode Island

We flew into Rhode Island and would be flying out of Rhode Island the following day. But in the meantime we had time to enjoy a long slow drive back with a stop along the way at Minuteman National Historic Park.

Attractions: Minuteman National Historic Park, MA : 4.5 Stars

Minuteman National Historic Park allows you to follow the path of Paul Revere and the patriots in the opening moments of the war on the road from Lexington to Concord. You’ll pass from house to tavern to farm along the route leading to the Old North Bridge and the site of the first battle of the Revolution in 1775. It was here that the first British troops died and was fired the “shot heard round the world”.

We spent a couple hours here and walked across the reconstructed North Bridge and found ourselves at the Old Manse. Earlier I mentioned that the kids learned a lot about Nathaniel Hawthorne on this trip and that is where the story continues.

Nathaniel Hawthorne rented the house from Ralph Waldo Emerson and he lived and worked with his wife there. The couple etched epitaphs in the glass panes of the windows which you can still read today.

In Concord we found a decent fast food Italian eatery for lunch then continued on to Providence, RI for the night.

Lodging: Comfort Suites, West Warwick, RI 4 Stars
This was a nice, comfortable hotel for our last night on the trip. We found the room clean and spacious with easy parking outside the room.

After checking in the weather began to shift dramatically and rain began to fall. Still we wanted to go out to dinner in Providence, RI.

Restaurants: Trinity Brewhouses, Providence, RI 4 Stars
Overall we enjoyed ourselves at Trinity Brewhouse. The interior is eclectic but rather fun. The food and brews were both good.

Day 8: Newport and Fort Adams

Our flight home was in the afternoon so we had the morning to see some of Rhode Island. We drove south to Newport and crossed the bridge to see the coastline. The wind was incredibly strong following the prior night’s rains.

We drove over to Fort Adams and because of and in spite of the weather we got a private tour of the fort by the navy veteran tour guide.

Attractions: Fort Adams State Park, RI 5 Stars

We were led all throughout the fort, given a thorough understanding of its history and construction, shown the cannons and how they were operated, and taken into subterranean dungeons. Overall just a really cool experience.

And with that a very memorable and fun vacation was over. The kids learned a lot and so did us as parents. We enjoyed the scenery and the history and the various forms of chowder. We saw and did a lot on this journey, but left a lot still undone, particularly in Maine. We’ll have to visit New England again in the coming years.

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