May 2025 – LongLegsBigCity

Three weeks ago, I went on a 3-day whirlwind road trip through New England, which seems as good an occasion as any to come back to the blog! We hit seven states from Monday at noon to Thursday at noon. That’s a lot of driving, and a LOT of snacks, as you’ll see. NY to CT to RI to MA to NH to ME and back to NH to MA to RI to CT to NJ to NY.

I thought about organizing this blog into places, activities and food, but that seemed more confusing, and less impressive than chronological, because I know you will be floored with the amount of ground we covered.

First question I repeatedly got: Where was your child? At home. With his other parent. And nanny. Praise the lord for our nanny. More on that another time.

Second question I got: Why? Because I was off work for the week and needed some girlie time. And my BFF was visiting from Australia. And I had never been to Maine.

We booked the car four days before setting off, and then the next day we booked three bed and breakfasts, the first in Bristol, Rhode Island, then in Kennebunk, Maine, and then in Madison, Connecticut. We didn’t plan or book anything else, but we created a Google Map with about 50 things pinned as possibilities. Many were closed for the season or closed on the random days we were going, but don’t you worry, we found a lot to do.

The main (pun intended) purpose of the road trip was to spend time together, so we knew that no matter what happened, we would have fun.

Our first step was to set up the car’s Bluetooth. I had driven a car the month prior, but before that, I hadn’t been behind the wheel for a year #CityGirl. Kat drives often, but on the other side of the road. We needed navigation help. Special shoutout to Google maps.

But more importantly, we needed playlists. Our jams varied from 2000’s pop to Lady Gaga’s new album, “The Most Hype Taylor Swift Playlist,” to the Wicked soundtrack, Boy Bands, and Simon and Garfunkel. Basically, only the best music.

Once we had a map and some songs on deck, we hit the road. We set our navigation for Mystic. Connecticut, and then started driving. We thought we would go to Mystic for lunch, but we found so many fun places to stop along the way that we didn’t end up in Mystic until nearly 5 pm.

First, we saw a billboard for the Pez factory. Excuse me? This did not show up on any of our research. ChatGPT didn’t mention it, Atlas Obscura somehow missed it, too. But thank God we saw that billboard while scream-singing The Wizard and I, because this place was AMAZING. Caps are intended, I could literally write an entire blog about this place. For starters, it was $5 to get in, and it came with a $4 coupon for merch. Then we were greeted with a scavenger hunt game to find and identify different Pez dispensers and spin the wheel for a prize. We were triumphant (with only a little bit of looking over kids’ shoulders)! I cannot recommend this place enough, we had so much fun!

We continued up the road and realized we’d be driving through New Haven. While Kat had been there before, I hadn’t! We had to make a stop and see Yale, where Rory went to school. Rory from Gilmore Girls, of course, our favorite show. More on that later. Yale was absolutely stunning. We first stopped at Cookie39 for some snacks to bring on our campus walk, and it happened to be Cookie Happy Hour, which I did not know was a thing, but I love that it is. We took our Cheesecake, Peanut Butter and Snickerdoodle cookies for a gorgeous walk across campus and to the bookstore, where we came across girl scouts selling (more) cookies, a first for Kat. Of course, since she hadn’t ever had any, we asked them for their recommendations and ended up with a box of Samoas. Kat was so excited to meet Girl Scouts in the wild, she had to take a photo.

We hopped back in the car ($1.50 for parking… clearly not in NYC anymore) and finally made it to Mystic Connecticut where we did some shopping along Main Street in the coolest stores including one shaped like a lighthouse where they were creating baskets and plates and earrings from knots. We had to try Mystic Pizza, where the Slice of the Day was Spaghetti and Meatballs. I can’t resist some carbs on my carbs, and I was not disappointed.

We continued north and made our way to Watch Hill aka the place of the one and only, Taylor Swift’s holiday house. We couldn’t believe our luck, but as we arrived, THE GATE OPENED and a truck went in. No, we didn’t see Taylor, but this was almost as exciting. Every home was more and more impressive than the next. And they were all completely empty in the off season. I’m still wondering how I can get that house-sitting gig. After a brisk walk to ogle the homes, we got back in the car and made it to our Bed and Breakfast, where the welcome board indicated that we were the only guests. Who else spends a random Monday night in Rhode Island in April? There were only two restaurants/pubs still open according to the B&B’s binder, so we quickly made our way to one and had THE BEST dinner. Also, it was $7 Martini Monday. We just kept winning.

The next day we woke up at our private B&B and had the loveliest breakfast chatting with the host. He gave me a great coffeehouse recommendation, and the food was just amazing. Homemade lemon bars, delicious yogurt parfaits, we did not want for food on this trip. We headed out again with no destination except our evening B&B, and again, we saw a sign that made us change course. We saw an exit for Foxborough, MA, and Kat said, isn’t that where the Patriots play? I couldn’t care less, since I’m an NCAA not an NFL girlie, but I do love exploring a stadium. We turned off the road, and Kat was in heaven. First of all, she loves a shop, and this was THE BIGGEST shop, not to mention that it turns out the stadium itself is kind of inside a huge outdoor mall. From there, we went to Newburyport, MA which was adorable. We found a candy shop called The Candyman, and we saw the actual Candy Men (the owners/founders) making their specialty: cashew turtles. We bought a few for the ride.

We went on to Portsmouth, NH, where we stopped for lunch and some more exploration. Kat found a restaurant called Cheese Louise, which originated as a food truck, and specializes in unique grilled cheese. It was AMAZING. After more exploring (read: walking off our millions of snacks before sitting in the car again), we headed to the Kittery Outlets, where we decided to spend the afternoon that was forecasted to rain. Unfortunately, when we got back to the car I had a parking ticket, which made me extremely mad because I paid for the spot!! Since our trip, I contested the ticket, and I was granted a “one time variance.”

We spent some money at the outlets, and headed to the next destination, the Nubble Lighthouse, one of the “most photographed lighthouses in the world,” on a rocky islet 100 yards off the mainland of Maine. The lighthouse was gorgeous, but the post-storm vibes and incredible opulent homes around it made it even better. We took many photos, shivering and slightly damp, and then we shuffled back to our car to head to our evening B&B in Kennebunk, Maine.

After a quick drop off of our things, we headed to The Pilot for dinner, where we had the best clam chowder I’ve ever eaten. I know that is an extreme statement but it’s true. We ate so much food, then returned to the B&B to eat the homemade cookies and Ghirardelli chocolate left by the host and cuddled in bed to watch Gilmore Girls together. It was basically the perfect night.

The next morning, we rose early again. I think it was a shock to my system not having to wake up overnight to feed a baby. I was up ready to rock and roll by 7 every morning! That worked well, because we had our longest day of driving ahead of us. But first, breakfast. Our host again made us the most incredible breakfast of French toast with fresh fruit, homemade granola in yogurt parfaits, and hot coffee. After taking photos in front of our B&B, which became a daily tradition, we walked next door to the famous Wedding Cake House to take more photos, and then we began our longest driving day.

Our goal for the day was to make it to our turnaround spot at THE BOOT at L.L. Bean and then drive all the way back down to Connecticut. Spoiler alert, we did it! L.L. Bean has a massive campus, especially because their main store is under renovations. They currently have 6 separate stores, one of which is a temporary massive tent, called Camp L.L. BEAN. I got two pairs of hand-cut shoelaces and fun stickers, and Kat got an embroidered Boat & Tote. We got a workout shopping at all of the stores and made our way to our first (3) snacks of the day. First up, the official snack of Maine, the whoopie pie! Did you know that? Because I didn’t. They had a store full of different flavors, and we tried chocolate peanut butter and pumpkin. Both were amazing. We then made our way down the street to McDonalds. If you’re thinking that is lame, you haven’t been to this McDonalds. Due to Freeport design laws, there are no big yellow arches to be found, they had to remodel an existing mansion and build a McDonald’s in it. The outside is an unassuming house, but the inside looks like a regular Micky Ds. Very strange. We hadn’t had enough snacks yet, so we went further down the street to Wilburs’s of Maine, where we watched them make chocolate-covered espresso beans, and bought some more treats for the road. We hopped back in the car, threw on some more Taylor Swift and started driving south.

We made a quick stop in Portland, Maine for lunch of lobster rolls and lobster mac and cheese, and went for a walk. We found the original location of SeaBags, a store we kept seeing around the northeast. Every bag and item in the store is made from recycled boat sails. They were so cool, and at the factory store we got a few items on mark down. We spent the rest of the afternoon in the car, but a road trip would not be complete without a Blizzard, so we made a mandatory dinner pit stop at DQ. Kat had never tried their chicken tenders, which are superior (shoutout to my nephew who introduced me to this), so thank goodness this DQ was a “grill and chill.” We took our Blizzards and tendies back to the B&B where we showered and tucked in for our final night of cuddling and Gilmore Girls.

Are you wondering why I have mentioned Gilmore Girls 3 times already? Well, because we are obsessed. When we were roommates, we used to watch it all the time, and even though we live on opposite sides of the world, we still talk about which episode we are currently watching, and why everyone should be #TeamLogan (kidding of course, we are only #TeamEmily).

Anyway, since we are obsessed with GG, the perfect end to our road trip was the places where GG was inspired by: The Mayflower Inn in Washington, CT, and New Milford, CT, the inspo for Stars Hollow. I am not really sure how to describe the feeling of stepping into a place you always wanted to visit/live/make friends/be townsfolk in. There were references everywhere to the show, like the antiques store where they said on the sign outside that they were “nicer than Mrs. Kim,” or the diner that had the same “NO CELL PHONES” sign as Luke’s Diner, and of course the infamous gazebo in the town square. I almost cried when we stepped inside. It was surreal and so special to be there with one of my closest friends. We ate at the diner (duh) and did some shopping before heading back to the airport for our “goodbye for now.”