Family Vacation Template: New England Road Trip

The worst part of a family vacation, other than unexpected kid tantrums, is planning and research. So we want to try something new on The Dad… Family Vacation Templates. When someone on our staff or someone in our community goes on a cool vacation, we’ll have ’em lay out the itinerary (transportation, hotels, restaurants, activities, etc.) along with some very light commentary. Maybe you were wanting to visit the same spot? You can pick and choose from the template, do what you like and sub out what you don’t, and save a ton of time (and maybe money)!

They don’t have to be road trips, or busy vacations, or expensive. They can be super simple! In fact, it’s encouraged.

First up…. a New England road trip: Boston->Cape Cod->Portland Maine->Bar Harbor->White Mountain National Forest->Boston.

Have you been to these places? Anything I should’ve done but didn’t? Would you like to do a similar writeup for a trip you went on recently? Email us at [email protected]

Background

Not all vacations are the same, and not all families are the same. Helpful to know the folks on this trip. My wife and I have two kids: a 10-year-old daughter and a 7-year-old son. They’re relatively flexible travels, as far as kids go. They aren’t always into overly active stuff like hiking, but they love swimming and experiencing new places. Your mileage may vary.

Day 1: Boston, Massachusetts

  • Flew into Boston Logan International Airport
  • Rented a car from Hertz Gold. Not an ad but I love Hertz Gold. Walk out, see your name on the board, pick any car. We let the kids pick. They picked a minivan. ????
  • Drove to Harvard
  • Alexander W. Kemp Playground. Pretty basic. But kids got some travel energy out.
  • Walked around Harvard. Visited Civil War Monument, Harvard Yard, John Harvard Statue, Harvard Square, Harvard Book Store. Bought some candy at Cabot’s Candy.
  • Drove to Fenway. Ate pizza at Woody’s Grill and Tap. Good pizza. (Just outside the restaurant, a dude stopped me on the street to tell me he loves The Dad! Love when that happens. If you see me, say hi!)
  • Walked over to Fenway Park and checked it out
  • Ate at The Barking Crab. Cool outdoor seating next to the water, traditional Boston seafood.
  • Walked over to Fan Pier Park. Not a lot for kids to do but we walked around and took in the cool views.
  • Walked back down to Children’s Wharf Park (currently under construction). Got photos with Hood Milk building (large milk jug for some reason?).
  • Got ice cream at Taiyaki NYC. Cool fish-lookin’ cones. Unique flavors.
  • Stayed at Seaport Hotel. Good city hotel with an indoor pool and fitness center. Location was awesome. We paid $345/night.
Fan Pier Park

Day 2: Boston, Massachusetts

  • Ate lunch at Buco Trattoria. More of a lunch spot for office workers, but pretty good. Had a small attached art gallery.
  • Boston Children’s Museum. Three floors. Lots to do for all ages. We stayed for several hours.
  • Took an Uber to The Paul Revere House. At this point, I had ENOUGH of Boston traffic. Depends on day/time of course, but we would’ve been better off walking. The Paul Revere House was slightly interesting from a historical perspective, just in sheer age of the structure and some stuff in it. But the kids definitely didn’t fully appreciate it and we weren’t there for long.
  • Walked down to Faneuil Hall Marketplace, did some window shopping. Lots of trinkets and touristy stuff. But also lots of food offerings if you want to try lots of stuff in one spot.
  • Ate at MIJA Cantina and Tequila Bar. This is a Mexican place in the market. Was actually super good. I picked the three most unique taco options on the menu and loved ’em all. My picky kids even liked the “crispy duck” taco.
  • Walked back to Seaport Hotel. Decently long walk for the kids but soooo much better than sitting in traffic. Saw the Boston Tea Party museum in distance.

Day 3: Cape Cod, Massachusetts

  • Drove to Cape Cod
  • Went to Seagull Beach. Nice, clean, pretty empty. Hardly any waves.
  • Ate lunch at Keltic Kitchen. They are known for breakfast food. Three words: CORNED BEEF HASH. Top notch.
  • Went to Veteran’s Park Beach. Had a good playground near the beach. My kids went in the water even though it was very cold.
  • Putt putt at Wild Animal Lagoon. Pretty standard family vacation putt putt. When in Rome, go putt putting. They did have this cooler of Dip N Dots style coffee ice cream though? Amazing.
  • Ate at TUGBOATS. $30 is a little pricey for a seafood sampler that literally has “Ritz crackers” on it, but cool outdoor seating overlooking the sun setting on the water.
  • Stayed at Hampton Inn & Suites Cape Cod. I’m sure there are better places to stay in Cape Cod but we honestly had trouble finding a good one. This place had free breakfast and indoor pool and hot tub. Did the trick. We paid $235/night.

Day 4: Drive up the coast to Bar Harbor, Maine

  • Drove up the coast
  • Stopped in Portland Maine at East End Beach on the Eastern Promenade trail. Loved this little town. Would’ve liked to spend more time there. Scenic and quaint. Saw a couple breweries and coffee shops. We just passed through. But this park had great views. We hiked around a bit.
  • Stayed at Holiday Inn Resort Bar Harbor – Acadia Natl Park. This hotel (or *ahem* resort, rather) was in a good location. The outside of the hotel was gorgeous. The outdoor pool overlooked the water in an almost infinity pool-esque way. Amazing. The staff was great. The rooms, however, were kind of stuffy and outdated. I’m not picky, but they didn’t give off a very clean feeling if you know what I mean. We paid $219/night.

Day 5: Bar Harbor, Maine

  • This was Father’s Day! I woke up and my entire family surprised me by wearing The Dad shirt. Hilarious and adorable.
  • Miss Samantha Lobster Fishing & Seal Watch Cruises. This was fantastic. We debated doing a 4 hour whale watching trip or this. We’re glad we picked this. The guides were great and it was very kid friendly and engaging. We saw a “pregnant lobster,” which even fascinated the naturalist (she hadn’t seen one before!).
  • Ate at Stewman’s Lobster Pound for lunch. This is a classic Maine thing. They had a “full lobster experience.” I did that. If you like lobster, pretty good! But for me, lobster is just so-so, and after seeing the “pregnant lobster”, it kinda grossed me out a bit tbh. But that’s just me. And I got a couple Thunder Hole Ales from Mid Atlantic Brewing and it was 100 emoji.
  • Drove up Cadillac Mountain and hiked a bit. As the highest point in Maine, this is the spot where the sun rises first on the United States each day. Pretty cool, and very accessible for families.
  • Went down to Sand Beach. Was overcast but still cool. Can’t say enough great things about Acadia National Park. So many great sights, especially if you like hiking, but even if you don’t.
  • Ate at Atlantic Brewing Midtown. Chill atmosphere and great food and beer flights. Plus rooftop dining!

Day 6: Bar Harbor, Maine

  • Next day hiked Jordan Pond from Trailhead to Bubble Rock Overlook and back. There’s a trail that goes up the east side of the pond. Maybe all the way around? Either way, hours of lovely hiking.
  • Ate at Jordan Pond House. Apparently, this is a must-do Acadia thing that we just stumbled upon. Glad we did. Good food. They’re known for “popovers“, which are spherical hollow pastry-like things that you put butter and jam on/in. Not bad.
  • Went to Wild Acadia. Kids were sick of hiking so we let them pick what we did in the afternoon. They chose this place they saw on the drive in that had a waterslide. They also had some ziplines and go-karts. It was… exactly what you would expect.
  • Walked across the Bar Island Land Bridge to Bar Island. During low tide, there is a sand bar bridge that becomes exposed. You can then walk across where the water used to be like Moses parting the Red Sea. It’s worth checking out! Make sure to time it right. My wife went for a jog and was out at Bar Island when the tide came back in and she had to wade through the water back to shore haha.
  • Ate dinner at Paddy’s Irish Pub. Actually a hotel restaurant. I got lobster bisque and it was ON POINT. But when is it ever not?
  • Walked to Mount Desert Island Ice Cream. Worth the .3 mile walk. Great flavors. I got “The Dude”, a white Russian flavored milkshake, with alcohol in it! We ate at the Village Green just outside the ice cream joint. A guy was playing violin and the weather was perfect. Quite nice.

Day 7: Drive through White Mountain National Forest, New Hampshire

  • Next day drove to New Hampshire. The drive itself was scenic. I took it all in while the kids watched a movie on the iPad. Ha.
  • Drove up Mt. Washington. This drive is no joke. It’s very tight, with no guardrails and very scary/steep ledges. I imagine if you are afraid of heights and/or not a great driver, you may panic a bit on the way up. On the way down, you CAN’T ride the brakes or they will overheat and fail. So take breaks. The peak was incredible though. Highest winds ever recorded were recorded at the top! They also have a cog railway that goes up it, but takes awhile.
  • Ate dinner at little pizza place called Pub 32. Great beer selection. Don’t know for sure but I feel we picked the best pizza place in town.
  • Stayed at RiverWalk Resort at Loon Mountain. This place was very nice. Huuuuge outdoor pool. Arcade. Winery. We hit up the winery for a tasting. I got the feeling the hotel was part of some sort of timeshare-style real estate investing salesy kinda thing. And I was scared we’d be solicited for some type of sales pitch while we were there, but thankfully it never came. We paid $250/night.

Day 8: White Mountain National Forest and drive back to Boston, Massachusetts

  • Hiked Flume Gorge. This was about 2 miles. But there was enough interesting stuff to see that the kids enjoyed it too.
  • Drove back to Boston airport