In early October, my mom, sister, and I took our annual mother daughter trip, this year with the cutest addition in tow, Rowan. Our annual mother daughter trips are usually 3 maybe 4 nights so this was the first time we’ve done an extended trip of 10 days. Regular readers know that my sister, Sarah, is a travel advisor so she planned the trip for us and did a phenomenal job! I love traveling in late September and early October because that is when I’m always so ready for fall but Charleston doesn’t quite catch up with fall until late October. As such, it is a wonderful time to get out of town in search of cooler temperatures.
This post is dedicated to our mother daughter fall New England road trip complete with our itinerary, highlights, photos, tips, and thoughts on taking a road trip with a 1-year-old. We took our trip in the fall but you could easily follow this itinerary in the winter for a cozy ski trip or the summer for some gorgeous outdoor time in the New England mountains and on the New England beaches! This post is lengthy because I went in-depth with what we did and our recommendations so be sure to save it if you’re planning a trip to any of the 5 stops below on our mother daughter fall New England road trip.
Our Mother Daughter Fall New England Road Trip
Sarah plans trips for her clients all around the world and makes life so very easy! Since having Rowan, extra time in my day for things like trip planning has been zapped, so I rely heavily on Sarah on this front. She’s traveled the world herself, is an absolute pro, and can secure hotel amenities, room upgrades, comped airport transfers (huge when traveling abroad!), free breakfasts, and more so consider her if you’re thinking about seeing the world again in 2022. More on Sarah here!
Prepare yourself for tons of photos! This post is a bit like a scrapbook entry for me from a wonderful trip so thank you for indulging me.
First Stop: 1 Night in Boston
My mom, Rowan, and I took an easy flight from Charleston to Boston where Sarah met us from California. We stayed at XV Beacon, which was fantastic because they have amazing connecting rooms (great when traveling in a group like ours or with kids) and the location is perfect! We walked everywhere! There are a handful of really great hotels in Boston that Sarah recommends for different reasons and different clients but we loved our stay.
In Boston, we wandered around Beacon Hill and Newbury Street, spent a lot of time playing outside and feeding the ducks in Boston Public Garden and Boston Common, had a delicious dinner with local friends at Saltie Girl, sipped coffee and nibbled on delicious breakfast treats from Tatte Bakery, enjoyed an easy lunch at Eataly (great for kids!), and thoroughly enjoyed the Isabella Stewart Gardner Museum. Sarah knew ahead of time to pre-purchase our tickets and reserve a time slot for us to visit the Isabella Stewart Gardner Museum (new Covid protocols), which we were so grateful for.
It hadn’t occurred to my mom or me and we wouldn’t have been able to visit the museum otherwise because it books out in advance. The museum was sensational and incredible to tour. It’s impossible not to imagine another world when walking through the historic home. A few Boston shops we enjoyed were Brattle Bookshop, Dress, the Follain flagship store, and Kodomo.
We all love Boston and agreed that we wished we have planned for a second night in the city because there was quite a bit more we would have liked to do.
On our way out of Boston, we visited the cute neighboring town of Weston to pay a visit to the Weston Table brick and mortar store. We are all avid shoppers of Weston Table so it was wonderful to see their store in person and to meet the founder who popped in while we were there. They were so cute and gave Rowan the sweetest little teddy bear!
If you aren’t familiar with Weston Table, then you’ll be happy to know them now. They have an incredible e-commerce site full of antiques, cookware, kitchen items, linens and textiles, drinkware, gifts, home decor, children’s toys, and more. I left with a new toy car for Rowan and a stunning antique oyster plate for me.
Second Stop: 2 Nights in Bretton Woods, New Hampshire
Since we opted to spend the majority of the day in Boston and visited Weston, MA, we arrived in New Hampshire at the Omni Mount Washington Resort at night after the sun set. We picked Bretton Woods, New Hampshire to be on our road trip route because of the grand, historic Mount Washington Hotel. It is a sprawling, old, historic, haunted hotel that you can just tell when you walk the halls has so many stories. It is definitely one of those “if the walls could talk” places. Fun fact: this is where the Bretton Woods Agreement was signed. It was so dark driving in that we had no idea what our surroundings were, which made waking up the next morning so exciting and breathtaking! Upon arriving, we had an easy dinner at the hotel’s more casual restaurant and turned in for the night.
On our full day in Bretton Woods, we really enjoyed the hotel and the surrounding area.
The sweeping views of the incredible fall foliage from the hotel’s grand wrap around porch is a sight worth seeing! Rowan also enjoyed some time with my mom playing around on the hotel’s vast grounds while Sarah and I each had separate afternoon conference calls. We also went just down the street to Mount Washington ski area and rode the gondola up to the top of the mountain for lunch. The views of the bright red, orange, and yellow foliage from the gondola were spectacular! We were riding through the trees and through the rainbow of leaf colors. It was a great activity to do with littles.
That night, we sipped warm ciders on the hotel’s porch and ate dinner at the hotel in their main dining room. We had connecting rooms here, which made it easy for my mom and sister to lend me a hand at bedtime and allowed me to easily go into their room with them in the hours between when Rowan and I went to sleep. It is definitely a very family-friendly hotel I’d say.
I also want to note a few other things on our Bretton Woods radar: driving the Kancamagus Highway, visiting the Crawford Notch State Park, popping by the Chutters Candy shop, and the Cog Railway Steam Train (I think this train would be so fun with kids a bit older than Rowan).
Third Stop: 2 Nights in Woodstock, Vermont
After our second night in Bretton Woods, we woke up, ate breakfast and checked out of the hotel (after I bought a snow globe from the hotel gift shop for my budding snow globe collection!). We made a few stops on our drive from Bretton Woods, NH to Woodstock, VT. We loved visiting Lonesome Woods. The owner is a super interesting chatty guy who has so many old Americana items in his shop. I wouldn’t call it a shop for serious antiques but everything he collects and curates makes you want to move to New England (think: old flags, pendants, books etc). It’s a must-visit if you’re in the area. He also has his own line of delicious candles that we all stocked up on.
The Maia Papaya coffee shop next door was great too! We also stopped at Harman’s Cheese and Country Store, which was some of our most favorite cheese we tried on the whole trip! They have a great online store and ship all over the country too. Their 3-year-aged cheddar was our favorite! Our final stop on the drive was in Hanover, NH at Dartmouth College. It was a home game day and Dartmouth’s homecoming weekend for their football game against Yale so it was a blast to see the campus in full Saturday fall football motion. We enjoyed lunch here and a walk around the college town to stretch out legs.
When we arrived in Woodstock, we checked into the Woodstock Inn & Resort before doing a big walkabout town.
This was my second time staying at the Woodstock Inn and I was so happy to be back. I just love that hotel (and their afternoon cookies!). The rooms are so well appointed, the common spaces are cozy and inviting, the food is great, and the location simply can’t be beat. The first night, we had dinner at the hotel in one of their restaurants, Richardson’s Tavern. We enjoyed the ease of a lot of dinners at our hotels because it was super convenient with Rowan. After dinner, my mom put Rowan down and Sarah and I did a nighttime ghost tour of downtown Woodstock. It was hokey but cute on a beautiful crisp fall night.
We packed a lot into our time in Woodstock!
Over the course of our full day there + the half day we spent the next day before driving to Manchester, we went to the Farmhouse Pottery flagship shop and studio, went to the Simon Pearce Glass Blowing Mill (highly recommend making a lunch reservation here too! Delicious!), walked the Middle Covered Bridge, did cheese tasting at Sugarbush Farm, visited the animals and attended a fall festival at Billings Farm, drove by the Sleepy Hollow Farm, grabbed coffee at Mon Vert Café, picked up nibbles at The Village Butcher, ate dinner at The Red Rooster, and window shopped at Yankee Bookshop, RT Home, Red Wagon Toy Co., F.H. Gillingham & Sons General Store, and South Woodstock Country Store (we had a delicious lunch here too!).
I just love Woodstock, VT so much. It is such an enchanting little New England town with tons of personality and a surprisingly lot to do! There is also a nearby incredible looking hotel that doesn’t allow children. I really want to go with Edwin one day (Sarah, I’ll be calling you!) to explore even more of the area!
On our drive from charming Woodstock to Manchester, we made one major pitstop in Weston, VT at the Vermont Country Store and the Weston Village Christmas Shop. They are right across the street from each other and quite iconic little Vermont establishments (especially the Vermont Country Store). As you can imagine, we came away with maple syrups and trinkets galore. Also on our radar for the drive were the JJ Hapgood General Store and the Maine Street Bakery next door but we decided to keep moving toward our final destination.
Fourth Stop: 2 Nights in Manchester, Vermont
Once in Manchester, we checked into the Kimpton Taconic Hotel. This hotel was just fine – absolutely nothing wrong with it but it didn’t have an IT factor or charming cozy nature at all. There are other hotels in the Manchester area that Sarah would recommend (including one that wasn’t very kid friendly, which is why we opted against it) but in general, I’d say Manchester was the only place on our trip that I didn’t just absolutely love. Before our trip, I had been to Boston, Woodstock, and Kennebunkport before so Bretton Woods, NH and Manchester, VT were the new-to-me spots.
I had loved everything I’d seen of Vermont previously so I was excited to stay in a new-to-me town. However, I just didn’t love it. There is good fishing (the original Orvis is here, which is neat!) and skiing nearby which would be a draw to return but otherwise the town is a hub for outlet stores, which felt a bit random. I will say that we hit the Herend outlet (it is closing its doors in spring 2022 forever) and that was a treasure trove but otherwise we skipped every single outlet store.
On our full day while staying in Manchester, we did do two outings that I couldn’t have enjoyed more though!
We went to the nearby town of Dorset, VT and I fell in love. It is a completely charming quaint little New England hamlet that is to die for in every way. It is little but so beautiful with a handful of yummy looking restaurants. In Dorset, we loved the Dorset Union Store, the 3 Pears Gallery (I bought a little painting for Rowan’s room!), Flower Brook Pottery, and In Stitches Needlepoint. There is a great historic inn in town and a beautiful old church with original Tiffany stained glass as well.
After exploring Dorset, we ventured over to Mad Tom Orchard to go apple picking. We picked so many delicious apples that we enjoyed on our car rides throughout the remainder of our trip! I have apple picked at a number of places in a handful of different states now and I can confidently say this orchard was the prettiest one I’ve ever been too. The views of the rolling hills covered in fall foliage surrounding the orchard were stunning! They had SO many apple varieties to pick too! I did love our dinner this night too, which was back in Manchester, at Ye Olde Tavern. It was yummy comfort food in a wonderful old home. I would recommend it if you find yourself in Manchester.
Other things on our radar for in and around Manchester that we didn’t get to do included touring Hildene, the Lincoln family home. I would have really liked to do this but it was closed the days we were in Manchester due to shortened Covid hours. There is also the Chiselville Bridge, the Equinox walking/hiking trails, the Equinox Valley Nursery, the Dutton Farm Stand and Berry Stand, Mt. Equinox Skyline Drive, the original Orvis store, and the Shaftsbury Alpacas.
Fifth Stop: 2 Nights in Kennebunkport, Maine
Our fifth and final stop on our fall mother daughter New England road trip was Kennebunkport, Maine. I had been to Kennebunkport back in 2015 with Edwin and was highly anticipating my return. I really love this little slice of the Maine coast. We checked into the marvelous White Barn Inn and were smitten right away. The location is perfection – close to town and the beach but not in the thick of it. The hotel property isn’t huge but it is really beautiful with firepits, a gorgeous pool, and nice little lawn. Our room was really spacious and so comfortable complete with a picnic basket delivery each morning of treats and coffee just the way we liked it. I want to come back and stay here again with Edwin!
After checking in, we set out to do a huge walk along Ocean Avenue. We started at The Colony Hotel and walked up past the Bush family compound and beyond before looping back. It was sunset during our walk and the most stunning seaside evening. It was pure heaven. We then headed into the town of Kennebunk (different than Kennebunkport) to have dinner at 50 Local. It was delicious and fun to see neighboring Kennebunk as I didn’t venture over there on my previous trip to the area.
The next day, on our full day in Kennebunkport, we had a fantastic breakfast at White Barn Inn before setting out on foot to do lots of window shopping and bopping around.
We visited Seacraft Vintage (obsessed!), Bulfinch Antiques (loved!), Daytrip Society Junior (super cute!), Snug Harbor Farm (obsessed!), Antiques on 9, Après Sea, Bliss, and Sea Love Candles (you can pour your own candles here too). We then had a glorious swim in the heated pool back at White Barn Inn before Rowan’s afternoon nap. That evening, we took a drive out to Goose Rocks Beach with nibbles to watch the sunset and to play with Rowan in the sand.
Our drive took us through Dock Square down along Ocean Avenue and then on to Cape Porpoise before hitting Goose Rocks Beach. I loved seeing Cape Porpoise and the fish houses in the area – so unique. We ended the day with dinner back at White Barn Inn. We ate in the more casual of their two restaurants. It was divine but I will say that their more fine dining restaurant looked incredible (not kid friendly so we didn’t go). I really want to go back with Edwin one day!
Also on our Kennebunkport radar that we didn’t get to were Parson’s Beach, Goochs Beach, apple picking at Spiller Farm, Frinklepod Farmstand, and lots of restaurants!
After our two nights in Kennebunkport, we made the easy drive back to Boston on our final morning and all flew home.
It was a wonderful trip full of quality time together, breathtaking scenery, endless exploring, antique hunting, yummy food and local cheese, and tons of opportunities to see the world through Rowan’s eyes that I won’t soon forget. Thank you mom, Sarah, and Rowan for giving me a whole new treasure trove of memories from this trip! Our mother daughter fall New England road trip was one for the books! To end this lengthy post, I have a few thoughts on what we would do differently if we were to do it all over again and thoughts on taking a roadtrip with a 1-year-old.
If We Were To Do It All Over Again
If we were to plan our mother daughter fall New England road trip all over again, we were all in agreement that we might have opted for less spots so we could spend more time in fewer places (this was particularly true because we were traveling with Rowan). For me, I’m so glad I saw and experienced The Omni Mount Washington in Bretton Arms but I don’t think it’s a place I need to rush back and stay. If I was in the area, I would definitely make a point to visit for lunch and porch views though. I also would have eliminated Manchester from our trip, although I did love neighboring Dorset and Mad Tom Orchard. However, it wasn’t far enough that I couldn’t have made a daytrip to the area if I was doing a longer stay in Woodstock, VT.
So, of our stops, I would have narrowed the trip down to Boston, Woodstock, and Kennebunkport and spent more time in each place. Nothing was too far away from anything so visiting the other spots wouldn’t be totally out of the question. I’m also looking forward to exploring Stowe, VT one day as it looks like a great little town. Is there anywhere else y’all think I need to add to my life travel list for the area! We’ve explored a bit more through Massachusetts, Maine, and Vermont over the years beyond the spots on this list that I also really love. There’s just so much to see in New England! Next summer, I’ll be in Newport, Rhode Island for the first time and absolutely cannot wait!
Thoughts on Taking a Road Trip with a 1-Year-Old
If your child is an excellent car sleeper, then a road trip is for you! Rowan is not a child that falls asleep immediately in the car so there was a lot of car time spent entertaining him when he wasn’t content himself with a toy, snack, or a bottle of milk. None of our drives were super long but I do wish we had put him through a little less driving. It was definitely a learning experience for me.
I will also say that all the in and out of the car would have been completely trying without the Doona. The Doona made everything possible and everything easy. I’ve said it before and I’ll say it again, if you plan to air or car travel a lot with babies, then the Doona is an absolute must! It is a car seat and stroller in one that easily collapses and saves every parent’s life.
When traveling with littles just be prepared to go with the flow and to get there when you get there. We took unexpected stops for more snacks, for playtime and crawling outside, and to change diapers. If you don’t have high expectations of arriving everywhere when you think you will, then you’ll be totally content and happy. My thoughts on taking a road trip with a 1-year-old are to just go with the flow and to enjoy the ride – planned and unplanned experiences included!
I hope you enjoyed this post on our mother daughter fall New England road trip and put it to good use to help plan a trip for yourself one day! xx
