3 Weeks In Massachusetts Not In Boston: Here’s What We Did

From mid-September to mid-October 2023 my parents came over from the UK to join us on the road trip for a month in New England. Their visit was bookended by Shae and I spending six weeks in Massachusetts – about three weeks in the Boston area, three days in Salem over Halloween and about three weeks in other areas.

Normally I write separate roundup posts for each place we visit to cover everything we did there. However, those three weeks in other areas weren’t our most productive in terms of travel experiences for a variety of reasons, so it made more sense to do one roundup post for all three places. (Edit: perhaps I should’ve written several posts after all as this end result is ~4,500 words!)

Here’s what we did in Conway, Wareham and Plymouth and why none of those places worked out as planned.

Where We Stayed

Conway

We wanted to spend some time in western Massachusetts and ideally would’ve stayed in Springfield seeing as it’s a bigger city with lots things to do there like The Amazing World of Dr. Seuss Museum. With it being the fall in New England though, hotel prices were expensive both cash-wise and points-wise.

I managed to find us this nice little Airbnb in Conway instead. It was a studio apartment beneath the host’s main house which wasn’t necessarily going to be ideal size-wise or noise-wise, but it worked out OK. We barely heard the host above us (and our dog Truffles certainly would’ve let us know if there was noise above us!) and there was enough space inside to not feel totally crowded.

So why did I actually pick this Airbnb then? A few reasons. One is that it was one of our most reasonably affordable options and even then it was $102.66 per night for a week-long stay which is more than we’d usually pay.

Another is that back in 2020, Shae had booked an Airbnb for my 40th birthday which had to get cancelled due to COVID. We’d forgotten we had a credit sitting on her account as we book all our stays through my account, but she’d booked that one through hers to keep it a secret for my birthday. Thankfully Airbnb had sent us an email earlier this year letting us know the credit was due to expire at the end of 2023. We’d already booked much of our accommodation for 2023, so this gave us an opportunity to use that credit to ensure it didn’t go to waste as this Airbnb in Conway was only a little over how much that credit had been for.

Another reason was that the Airbnb was near the seemingly-cute village of Shelburne Falls, so that would give us somewhere nice to visit nearby. Finally – and most importantly (for Shae particularly) – the Airbnb host has a couple of goats on property who you can say hi to, feed carrots, etc.

Wareham

Just before my parents arrived, we had a five night stay booked in downtown Boston. Between Conway and Boston we had a five day gap of time to find somewhere to stay. Again, with this being New England in September prices were expensive, but Wyndham’s partnership with Vacasa (a vacation home rental company similar to Vrbo and Airbnb) came to the rescue.

Wyndham charges 15,000 points per night per bedroom at Vacasa properties (reduced to 13,500 per night if you have a Wyndham credit card) and we found this one bedroom property in Wareham that looked like it would be lovely to stay in. Wareham is an hour south of Boston just before you enter Cape Cod, so it would also be a great launching point for visiting places like Plymouth just to the north and Provincetown on Cape Cod.

Things didn’t start out well though. We arrived at the Vacasa property and got inside, only to discover that it hadn’t been cleaned since the previous guests. The bed wasn’t made, towels and sheets were strewn on the floor and there was more dog hair all over the hardwood floors than I’ve ever seen before.

I immediately got on the phone to Vacasa to report this. Shae had a very poor experience at a Vacasa property in Wilmington, NC last year and customer service from Vacasa was awful, so I wasn’t holding out much hope. The guy I spoke to said he’d report the problem to someone more local, but didn’t give any sense as to whether any kind of prompt resolution would be forthcoming.

Thankfully, just as my phone call with him was about to end, the cleaners showed up. They said that it would take about an hour for them to clean the property. Even though it was only a one bedroom cottage, I thought that was a little optimistic, but we took them at their word and went to the grocery store before returning an hour later.

Sure enough, they were just finishing up and the place was absolutely spotless. It obviously would’ve been nice if we’d arrived to find the property that way initially, but we appreciated that they got everything cleaned so thoroughly and so quickly.

Now that it was clean, it looked much better. The cottage is located right on the Sippican River and is nautical themed. It’s incredibly cute and was a fantastic spot to spend five days. Although there were neighbors nearby and grocery stores and restaurants just a few minutes away, it felt more rural there.

Despite the initial cleaning mishap, we adored our time there and would happily return.

Plymouth

The third and final place we stayed in Massachusetts that wasn’t Boston was Plymouth. We hadn’t planned to stay there originally, but rebooked things after Shae realized there were lots of interesting-looking museums nearby.

It was early November by that point, so hotel prices were starting to drop now that peak fall season would be over, although they still weren’t cheap. Our best value option ended up being the Holiday Inn Express Plymouth using IHG One Rewards points.

I booked us an eight night stay there because IHG gives every 4th night free on award stays for people with the IHG Premier, Traveler or Business credit card. That meant we’d get both the 4th and 8th nights free, plus we get a 10% points rebate thanks to also having the old IHG Select card. That made our net cost 16,313 points per night; we’d bought those points for 0.5cpp (cents per point), so it effectively cost us $81.57 per night which was great value considering cash rates at this hotel and other nearby properties were $150+ per night.

Our room was a good size with a king bed and chaise lounge. I thought the chaise lounge was a weird design choice considering they could’ve fit a couch in the room. The windows could also be opened which isn’t something that I’d normally bother mentioning, but that ended up being a huge benefit during our stay – more about that in the next section where I explain why we didn’t really do anything in Plymouth!

As for the hotel itself, it was a bit of a mixed bag. The shower was excellent as it had fantastic water pressure and there was a guest laundry area. They had a decent complimentary breakfast with several hot options each day that ran until 9:30am on weekdays and 10am at the weekend – something I appreciate as a late riser.

There were a few things that weren’t as great though. The indoor swimming pool was fairly chilly, so it wasn’t surprising that no one ever seemed to be in there. The fitness room was sparse with only three pieces of cardio equipment. An annoying feature was that we had to reconnect to the internet every 24 hours. It felt like it always disconnected right when I was in the middle of something, so that was frustrating.

Service wasn’t all that great either. Shae had flown back to Virginia for a couple of days to see her day who was about to have some major surgery. She had an issue with her rental car and was trying to get hold of me, but my phone was on silent. She therefore called the hotel and asked to be put through to me, but the front desk agent refused to do that. She wouldn’t connect her through to my room and didn’t even let me know herself that my wife was trying to get hold of me urgently. I’ve no idea what her problem was, but that was weird as she’d seemed nice enough when checking in.

What We Did

Conway

Historic Deerfield

Did you know that you don’t have to be over 50 to be a member of AARP? Shae and I have been members for close to 10 years as it’s so cheap and there are some benefits that can save us more than the nominal cost of membership each year (I wrote about 10 of them over at Frequent Miler).

One of those is that you can easily earn points with AARP Rewards. You have to redeem a huge number of points for a $5 gift card for select retailers, but a much better use for those points is to redeem them for discounts at local attractions, restaurants, etc. Are you familiar with Entertainment books you used to get (and possibly still get?) at grocery stores? The ones that have things like “Buy one entrée, get one free” or “Buy one museum admission ticket and get another free”? Well, Entertainment.com powers the local offers that AARP Rewards has.

Whenever we’re in a new place I enter the zip code of that location to see if there’s anything interesting nearby that we could save money on. Sure enough, while staying in Conway I saw a BOGO ticket offer for Historic Deerfield, so I redeemed 500 points to take advantage of that offer. For what it’s worth, it normally costs something like 15,000 points to get a $5 gift card, so redeeming 500 points for a free ticket costing more than $5 was significantly better value.

Historic Deerfield is listed as a National Historic Landmark District and features almost a dozen historic house museums with different types of exhibits in each one.

Unfortunately the attraction didn’t end up being quite what we were expecting. We were picturing it being more of a living history museum, but that wasn’t the case – at least not the day we visited. Many of the houses/museums were closed for renovation and/or restoration and the one or two that we went inside of which were open didn’t hold much interest.

The village itself is pet-friendly, so we’d brought Truffles along so that she could get out of the studio Airbnb too. Pups aren’t allowed inside the buildings (which is fair enough – we weren’t expecting that to be the case), but it was a hot and humid day, so all the walking around outside wasn’t as appealing after a while either.

In hindsight, we definitely should have just driven the 45 minutes down to Springfield to check that out instead.

Bridge Of Flowers

In the nearby village of Shelburne Falls, they have an attraction called the Bridge of Flowers. The bridge was built in 1908 to help transport goods that had been delivered at the nearby train depot. It didn’t get used for long though due to the blossoming popularity of automobiles at the time.

A member of the local women’s club suggested that the bridge be converted into a “Bridge of Flowers”, stating “If it can grow weeds, it can grow flowers!”

So that’s what the village did and the tradition has continued for almost 100 years since.

The bridge is open from April 1 to October 31 each year, although there was a sign when we visited in September 2023 that the bridge will be closed during all of 2024 in order to conduct repairs. It therefore won’t be reopening until the spring of 2025.

Something to be aware of if you travel with pups is that dogs aren’t allowed on the bridge. That’s fair enough as I imagine there would be numerous non-responsible dog owners who wouldn’t pick up after their dogs, plus they wouldn’t want dogs peeing all over the plants and flowers. We had Truffles with us when we visited, so Shae and I took it in turns to walk across the bridge while the other stayed with Truffles.

Shelburne Falls

Shelburne Falls is a cute little village of fewer than 2,000 people. We took a wander around after checking out the bridge, stopping at the falls from which the village takes its name.

Shelburne Falls Glacial Potholes

On the rocks next to the falls you can see naturally formed potholes. These glacial potholes along the Deerfield River were formed ~14,000 years ago. In years gone by you were able to swim in the pools, but that’s not allowed anymore.

Wareham

Our five days in Wareham were mostly spent catching up on as much work as possible before my parents arrived from the UK a week later. However, we did take a fun day trip out to New Bedford.

New Bedford

New Bedford was once the wealthiest city in all of the United States per capita. That’s because in the first half of the 1800s it had a huge whaling industry. Many towns that have long-gone industries like that fall into disrepair, but New Bedford is still a remarkably quaint city with cobblestone roads, well-kept brick buildings, beautiful public artwork and more.

New Bedford Whaling National Historical Park

Due to its important history, New Bedford Whaling National Historical Park has been established in the downtown area and covers more than a dozen blocks.

The National Park Service offers free guided tours at 2:15pm Wednesday-Sunday from May-October. Shae and I went on one of those tours and can highly recommend it. The guide was fantastic – she was incredibly knowledgeable about whales, the city’s history and just enthused passion about the topic which always makes a subject far more interesting and engaging.

The tour included stops at the New Bedford Whaling Museum…

…the historic Double Bank Building which, as the name suggests, featured two banks (one for wealthy merchants and one for everybody else) but which is actually two building constructed by two different builders…

…the Mariners’ Home which was used to help feed and shelter seamen with no money when they weren’t out at sea after being donated by Sarah Rotch Arnold who was the daughter of a wealthy whaling merchant…

…and Seamen’s Bethel, part of New Bedford Port Society.

Seamen’s Bethel was built in 1832 to serve as a church for the influx of seamen who spent at least some time in New Bedford while not out at sea. Local Quakers had been concerned about the conduct of the seamen as they would get back to port and blow all their money on alcohol, gambling and in brothels. The construction of this non-denominational chapel was therefore done to try to help guide them down a different path.

One of the people who attended services at Seamen’s Bethel was Herman Melville who wrote Moby Dick. In fact New Bedford features as a prominent setting in the novel.

Plymouth

Shae and I didn’t actually do any activities while staying in Plymouth. The reason why was that she got back from a quick visit back to Virginia to see her dad and discovered that she had COVID.

I’d gotten it for the first time a year ago and it knocked me out. This was Shae’s first time getting it and it laid her up in bed for the entire week too. I therefore didn’t go out to do anything myself because:

a) I didn’t want Shae to miss out and figured we could always return to Plymouth for a visit in the future

b) I was concerned that I might catch COVID from her but wouldn’t be testing positive yet, but could pass it on to other people nevertheless, and

c) I had so much stuff to work on, having an excuse to hole up in a hotel room for a week didn’t seem like a bad idea.

In an ideal world I’d have gotten a separate room so that Shae could self-isolate. However, the hotel we were at had no more award availability, cash prices were too high for our budget and nearby hotels had the same issue. We were able to help mitigate the risk of my catching COVID from her though by a couple of means.

Probably the most important element was being able to open our windows. This helped keep the room well ventilated, especially because it was so breezy outside during our stay. The heater in our room worked well, so we were able to keep things at a comfortable temperature.

It was also helpful having the chaise lounge as I slept there, with Shae on the opposite side of the king bed so that we’d have some good distance between us at night. The chaise lounge wasn’t very long, but the office chair was at the perfect height for me to rest my feet on at night. It might not sound comfortable, but I slept soundly all week; moving every week for the past 6 years has meant I can adjust to pretty much any bed and sleeping environment!

The good ventilation and staying apart despite being in the same room did the trick as I tested negative for COVID, while Shae eventually got better by the time it came to leave.

We’d actually stopped in Plymouth on our drive down from Conway to Wareham because at the time we didn’t have any plans to stay there. Here’s what we saw during that brief visit.

Plymouth Rock

Perhaps the most famous site in Plymouth is Plymouth Rock where the Pilgrims from the Mayflower are said to have disembarked from their ship. Plymouth Rock is likely more of a legend than a piece of factual history though as the first time someone claimed Plymouth Rock as the place that the Pilgrims landed came more than 120 years after the event.

As you can see in the photo above, it was pretty foggy the day we visited. Plymouth Rock is housed in an impressive Greco/Roman-style structure which, to be honest, oversells the impressiveness of what lies within. Ultimately, Plymouth Rock is a rock that isn’t as large as you might expect it to be, although it does weigh an estimated 10 tons.

The rock split into two pieces in 1774 when it was being moved. The two pieces were housed separately, but were later reunited and sealed together, with an inscription saying ‘1620’ on the larger side.

Plymouth Rock is thought to have once been significantly larger. However, chunks were broken off that people either kept for themselves or sold off, although it’s about 150 years since that last occurred.

At the top of a mound in front of Plymouth Rock is a statue of the Native American Massasoit.

Near that statue is Coles Hill Burial Ground. This features a monument dedicated to the passengers of the Mayflower at the site where they were first buried.

What We Ate & Drank

Conway

Conway is a small town, so we didn’t go out for a meal while we were there; instead, we just made all our meals at our Airbnb. We did get a drink and a snack while out and about though.

Black Birch Vineyard

After a somewhat disappointing experience at Historic Deerfield, the day redeemed itself when we stopped for wine tasting at Black Birch Vineyard.

They’re pet-friendly inside and out and have their own friendly pup and cats. The wine tasting cost $12 per person and you get to try five of their wines which are pre-selected.

We enjoyed all five, but liked the final red the best – Resolute Red. We therefore got a bottle of that so we could enjoy a glass outside before taking the rest of it back to our Airbnb.

Baked

While in Shelburne Falls, we walked past a bakery/café/restaurant called Baked. We couldn’t resist stopping in to grab a cookie as there was one that particularly caught our eye – a chocolate cayenne cookie. We’ve had cayenne in chocolate bars and loved it, so we were curious what it would be like in cookie form.

As it turns out – just as delicious!

Wareham

Moby Dick Brewing Co

After finishing our guided tour at the New Bedford Whaling National Historical Park, we decided to stop for a quick drink and snack at Moby Dick Brewing Co because how can you resist not stopping somewhere named that in New Bedford?!

The tour had been pet-friendly (they let Truffles come inside the buildings provided she was in her K9 Sport Sack (our affiliate link) that we’d brought with us), so we were pleased to see that Moby Dick Brewing Co has a pet-friendly outdoor patio. The weather was perfect that day, so it was lovely sitting outside.

Shae got what I think was a Whaler’s Punch which has dark rum, white rum, amaretto, triple sec, fresh lime, orange and pineapple juices  – she enjoyed that.

I ordered a flight of four beers – their Oktoberfest, Captain Boomer’s Blueberry Ale (which had blueberries floating on it too), Glorious Goney (a porter) and Whale’s Jaw (an American white ale). All four beers were good, with the porter – as expected – being my favorite as I prefer darker beers.

To tide us over until we got back to our Airbnb for dinner, we both got a Portuguese stuffed quahog to try. I’d never had a quahog before; the extent of my knowledge of quahog being that it’s the city where Family Guy is set!

In case you’re not familiar with quahogs (like me), they’re a type of clam. I therefore have zero clue how our Portuguese stuffed quahogs at Moby Dick Brewing Co compare to stuffed quahogs elsewhere, but we both thought it was very tasty.

Plymouth

Mayflower Brewing Company

After finishing up our three days in Salem, I’d dropped Shae off at Boston airport in the morning for her to fly back to see her dad. I then drove down to Plymouth and arrived too early to be able to check in at our hotel.

To kill some time – and to get some work done – I drove the couple of miles to Mayflower Brewing Company. They don’t serve food, so they’re pet-friendly inside which was awesome seeing as I had Truffles with me as we didn’t have a hotel room at the time I could leave her in.

Mayflower Brewing Co has an excellent selection of beers for all kinds of tastes. Some breweries only have one darker beer, so I was very pleased to see that Mayflower had several.

Any time a brewery has an option for a flight that’s what I go for so that I can try a variety of their beers. Many beer flights let you pick four, so it was nice that Mayflower lets you pick five.

I got their:

• Leisure Mode – a light & hazy New England IPA
• Pursuit of Sappiness – a maple syrup brown ale
• Thanksgiving ale (I think this was an Oktoberfest)
• Oatmeal stout
• English-style porter

All five of the beers were very good. I’d assumed that the oatmeal stout or porter would be my favorite, but in fact it was the Pursuit of Sappiness which was the best one I tried. I don’t think I’d ever had a maple syrup brown ale before, but it’s one I’d love to have again. I would’ve gotten to have it again too if it hadn’t been for that pesky COVID Shae got!

Tree House Brewing Company

I write part-time for Frequent Miler and a reader reached out when seeing we’d be in the area near where he lives, asking if I wanted to meet up for a drink. We ended up meeting up at Tree House Brewing Company; they have more than one location – the one we went to was their taproom in Sandwich (about 20 miles southeast of Plymouth).

We met up in the evening which was a little bit of a shame timing-wise as apparently the brewery has fantastic views of Cape Cod Bay during daylight hours. Despite not getting to enjoy the views, it was a great evening. It was fun getting to know Greg (not Greg the Frequent Miler!) and Tree House’s beers were excellent. They don’t offer flights, so I started off with their Daze which is an IPA.

That was tasty, but even better was their Nervous Energy – a milk stout. I’ve had some watery, not very flavorful, milk stouts in my time – this certainly wasn’t one of them.

Tree House Brewing Co has canned cocktails available, so I thought I’d take Shae there once she got back from Virginia as I figured she’d like it there too, especially during the day with views of the bay. Alas again though, that wasn’t meant to be – at least not during that visit anyway. Hopefully we’ll make it back to Plymouth in the future.

Things We Missed

Due to our busyness and sickness, there was a lot we missed out on all around Massachusetts. Here are some of the things on our potential to-do list for the future:

• Several museums in Plymouth
• Provincetown – there are whale watching tours, including some that are pet-friendly
• Cranberry bog tour
• The Amazing World of Dr. Seuss Museum
• Springfield Science Museum
• Lizzie Borden House
• Kennedy Compound
• Marconi Beach – pet-friendly
• Alden House Historic Site