Come Fly with Me: Four States, Five Days, Six Kids

Oct 12, 2021 at 11:28 am by RMGadmin

Our New England Fall Itinerary With Jenny Reimold

FALL BREAK…the one-week break from school that I had never been invited to, having lived most of my life in Florida. Not until we moved to Tennessee did I see those glorious days on the school calendar. Although I thrive in saltwater, and the Gulf Coast is the most popular vacation destination for most of my Nashville friends, I wanted to see FALL!!

FOUR STATES, FIVE DAYS, SIX CHILDREN…. Massachusetts, New Hampshire, Vermont and real itinerary, no real plan. Just a family of eight, traveling around New England in an industrial passenger van, missing turns and doing circles. Walking under covered bridges, making pies from farm-picked apples, and taking daily, scenic road tips was a refreshing and renewing family experience. So, if you have never been to the Northeast in the fall, plan on it. Don’t be too busy when you’re young to be too tired when you’re old. Book the flight. Rent the van. Follow in our footsteps. 


We flew into Boston and rented a 1750’s farmhouse/horse farm in Rowley, Massachusetts, about 45 minutes from the airport. (We went from October 5th – 11th). The house was renovated in 1990 and owned and used as a weekend getaway by a prominent female doctor who was starting riding as an older adult. Although the house had some additions, that very kind property manager let us know that the house had some “character” with sloping floors, low ceilings and was not baby-proofed, which we somewhat expected given the age. We traded some stink bugs for mornings feeding apples to horses on a beautiful farm. Given the size of our family, we prefer staying in homes, and if you are used to more bells and whistles, this may not be for you. 

Rowley, Ipswich and Essex are all north of Boston, close to the coast, and are in close proximity for multi-state drives. Rowley was roughly thirty minutes to Salem, thirty-five minutes to Maine, thirty minutes to New Hampshire, and two and a half hours to Vermont. 

Day 1: Portsmouth, NH & Salem, MA

Salem, MA
Portsmouth, New Hampshire

Following our morning in Salem, we drove thirty-five minutes north after lunch to Portsmouth, New Hampshire. Guided by my friend from NH, we toured Strawberry Banke, a ten-acre settlement on the river bank. Costumed interpreters and artisans demonstrated period crafts, cooking and boat-making techniques. I thought it was interesting, but naturally, my younger kids just wanted to go to Market Square for ice cream. 

Next to Strawberry Banke, Prescott Park has gorgeous foliage and flowers, while the self-guided Black Heritage Trail is an educational must-see. Portsmouth was a landing point for slaves, and the trail begins on Long Wharf, where slaves were auctioned. It walks you through stories of skilled artisans, abolition leaders and free slaves who helped build the town. 

Portsmouth is a compact town with a classic white lighthouse; most tourist attractions are close together by the visitor’s center. The coastal drive-in is beautiful and worth adding to your New England bucket list. 


Most famous for the notorious Witch Trials of 1692 and as the setting for the movie Hocus Pocus. Our family first drove to Salem and tried to explain to my children what happened in this infamous town as a former American Lit teacher. Then, we toured the city’s charming brick streets, ate lunch at Rockafellas (try the mac n’ cheese), visited Nathanial Hawthorn’s House of Seven Gables and took several photos in front of the Hocus Pocus movie sites. 

We also went to the Salem Witch Trial Museum, and although I had been there before, I had forgotten how scary it was. The life-size, animatronic Devil beast 

and exorcism scenes had us looking for the exit five minutes into the theater. While I think the museum is a must-see in Salem, I don’t think it’s really appropriate for younger children. Same with the ghost and cemetery tours. 

The town of Salem really goes all out for Halloween with parades, balls and special tours. Check local calendars for special events during your trip.  

Day 2: North Andover, MA

Be sure to add this one to your fall road trip! Smolak Farms is a 300-year-old, working family farm transformed into an educational and seasonal destination in New England. Not only is it a popular place for school field trips but also a beautiful wedding venue. With farm tractor tours of apples, plums, berries, pumpkins, Christmas trees and peaches, and orchards where you can pick your own fruit, this is a farm you don’t want to miss! 

After an afternoon on the farm, time spent in the petting zoo talking to llamas, a stop in Smolak’s incredible market, and too many free apple cider donuts, we returned to our rental to bake fresh apple pies. Of course, the horses at our farm rental were also more than happy to snack on our leftover fruit!


Day 3: Framingham, Boston 

Boston, one of my favorite cities in all of the USA! My husband spent most of his MLB career with the Baltimore Orioles, and I NEVER missed a road trip to Fenway. If you are there at the end of September or early October, try to get tickets if they’re in the playoffs. Hands down my favorite ballpark because of the atmosphere, the people and the food!!

The weather proved a bit rough for a Duck Tour, so we opted for the New England Aquarium instead. All of my kids, including my teenage son, loved this one, and we got through it in about an hour and a half, which left us plenty of time to walk the Freedom Trail downtown. As a mother of seven, I cannot recommend the Trolley Tours enough. Hop on and off and see all of Boston’s historical sites that your children will study in school, or just rest your feet and see where Paul Revere rode into town, the site of the Boston Tea Party, Harvard, the Cheers Bar, and Boston Common. There’s so much to do in Boston. Check other blogs and guides for your particular interests. 

To end our day, we gifted my husband a birthday surprise of GOAT YOGA at Goats to Go. On my Instagram, I have a habit of putting my professional 6’4” athlete husband in situations a bit out of his comfort zone, and I thought this sounded like the “perfect” present. So, complete with matching family headbands and a special spandex workout outfit for dad, we laughed for 2 hours as we posed and giggled through our goat yoga session and then took the goats on a sunset hike on the farm! This was a once-in-a-lifetime experience that had my family laughing for hours! 


Day 4: Vermont

This was the farthest destination from our rental. We left around 7 am to get the most out of our day in Vermont. We started our day in Woodstock, a town named as one of the best places to visit at Christmas and one of the best towns in America. Home to the Woodstock Middle Bridge, a beautiful covered bridge in the center of town, this quintessential Northeastern town looks like the backdrop for any Hallmark movie.

The charming downtown is home to many small boutiques, restaurants and specialty shops like The Red Wagon Toy Company, a children’s shop favorited by our family. In addition, Billings Farm and Museum is a top-rated family attraction in Woodstock that you should also add to your itinerary. 

While in Woodstock, be sure to stop (or even stay) at the Woodstock Inn. Set in the heart of Main Street, the historic, luxury resort features farm-fresh cuisine, wood-beamed ceilings, impressive gardens and golf. For lunch, we stopped at Mon Vert Café, a popular breakfast and lunch spot known for sourcing its ingredients locally. Finally, on our way out of town, I had to see Farmhouse Pottery. You’ve probably seen their pieces all over Instagram. Their pottery is all made by local artisans, and while you’re shopping, you can see each piece being made. While I shopped for unique items for my kitchen, my children stood at the windows of the pottery studio and watched how these gorgeous pieces were made.  

One last stop in Vermont….the famous pink house on Pinterest that a grandfather painted pink for his first granddaughter. Located across from Faulkner Park on Mountain Ave, we saw the owner pull up, and it was clear that he was accustomed to people taking photos of his beautiful Dutch Colonial home. 

Next in Vermont, an educational detour to President Calvin Coolidge’s homestead in Plymouth. This small, hidden village in the Green Mountains and the drive-in alone is worth the trip. Not only can you see where Coolidge was born, but you can also see where his father, a notary public, swore in his son as president in the family parlor when they learned of President Harding’s death. Also on-site, Plymouth Artisan Cheese, the second oldest cheese factory in the country, was founded by Colonel John Coolidge, father of President Coolidge. We also went to Coolidge’s gravesite just a few miles away, where the entire family was buried. 

To end our day in Vermont, we drove to Sleepy Hollow Farm in Pomfret, one of the most photographed farms in the country. The 115-acre farm is located on Cloudland Road and was recently sold by the previous owner, Aerosmith guitarist Joe Perry, for 2.2 million. We conveniently arrived at sunset, and there was a long line of cars parked along the side of the road to take family photos. This farm was listed on every fall foliage tour on Pinterest and is an incredible way to end the day in Vermont! On the way out, look for the red, Taftsville covered bridge. We pulled over to enjoy one last memory of our day in Vermont. 


Day 5: Maine

Our final full day in the Northeast was spent in Kennebunkport, Maine, famously home to the Bush family compound on Walker’s Point. This incredible coastal town in Southern Maine is known for fishing, shipbuilding and outdoor activities. Spend the day in Dock Square picking up local souvenirs, join a food tour with Maine Foodie Tours or hop on Rugosa lobster tour for a scenic tour of the beautiful coastline. Watch them haul lobster traps or join in the fun! (Unfortunately, the tour was booked, and my husband missed out on my idea of turning him into a lobster fisherman for the day. 

Our favorite part of Kennebunkport was the shorelines, where my family spent hours exploring the tide pools amongst the rocks. We followed suit with other tourists, pulled over on the side of the road near the Bush compound, and followed the sidewalk to some trails that allowed us to walk down to the shore. The views were incredible, and we left Maine with plans to return for a longer trip. 

The Dalai Lama suggests, “Once a year, go somewhere you’ve never been before.” Who are we to argue with that wisdom? A plane ticket or road trip to New England is the answer. Who cares what the question is?


Designer & Media Stylist

Writer and Franklin resident, Jenny Reimold, is a local designer who serves as HomeGoods’ “Style Expert.” Her work has been featured
in House Beautiful, HGTV, People Magazine online, Property Brothers and Good Morning America. To follow her work, visit her Instagram @jennyreimold.