Fall — Blog - Traveling Newlyweds

Disclosure: This post is sponsored by Enterprise. All thoughts and opinions are our own.

We’re big fans of fall.

Leaves changing, cozy layers, pumpkin spice lattes, snuggling by the fire… call us basic (and we are), but we love it. There’s something so heartwarming and life-giving about this time of year, and if anything, it means we’re that much closer to Christmas! (Only 62 days away - but who’s counting?)

We just returned from a big 40-day road trip throughout the U.S. We drove through national parks, coastal beach towns, metropolitan cities, and everything in between. Our last stop, and the true cherry-on-top of the trip, was a two-day visit to Lexington, Kentucky. The weather was crisp, the colors were changing, and the scenery could not have been more picturesque. But what really took our time in Lexington to the next level was renting a car from Enterprise.

We’d been driving our trusty little Prius for thousands of miles and were desperate for some space. It was such a treat to have a newer, larger, and plusher vehicle to explore in, and the entire Enterprise rental process couldn’t have been easier! We dropped our Prius off to get serviced, and the Enterprise rental location was only a short walk away. We walked in, checked in at the counter, found out they were giving us an upgrade (oh no, hehe), and within minutes we were sitting in our spacious Nissan Armada. No disrespect to the Prius, but this was a SERIOUS upgrade. Comfortable seats, space in between us, incredible audio… can we just trade?

Family photo! Can we keep the Armada and ditch the Prius?

One of our favorite things to do in a new destination is to drive around with no real agenda, and that’s exactly what we did. We stumbled upon charming estates, rolling hills, picturesque farms and stables, and even a castle! (WHO KNEW!) When we wanted to pull over, we would - even just to say hi to some friendly horses that were eagerly following our car. Even our pup Sally got a kick out of it!

A luxurious ride calls for a luxurious hotel… castle anyone?

Found a cute little lunch spot and Sally thought the burger was for her :)

Being that it is bourbon country, we also stopped at a few distilleries, whose grounds were just as beautiful and enchanting as the many estates we’d passed. (Two of our favorites were Woodford Reserve and Buffalo Trace - which also happens to be dog friendly!) We found quaint little cafes scattered throughout the countryside, many of which looked like something one would find in a Hallmark movie… it was all so picturesque!

Woodford Reserve has a stunning property!

Sally couldn’t taste bourbon, but she made friends.

Those couple of days adventuring through Kentucky were absolutely dreamy and ended up being exactly what we needed. And the biggest blessing was getting to do it all in our spacious Enterprise rental car that we jokingly named George. We still talk about George and how much we loved him. It was an experience we won’t soon forget!

Friends. We found fall. Not the kind of fall we experience in Southern California, i.e. “iced” pumpkin spice lattes, “light jacket” weather, and approximately ten total trees changing color (and you have to hunt for them).

No, the kind of fall that we’ve only seen in Hallmark movies. Trees with bright yellow, red, and orange leaves, apple picking farms, and crisp, cold air. We’ve officially been ruined by fall in New England. Here’s what we did in the hopes you can experience it one day too…

BOSTON

Now, we were only in Boston for a total of 18 hours, but we did it well (and we’ll be back). We stayed at the Beacon Hill Hotel, located in the picturesque neighborhood of Beacon Hill. We LOVED this spot. You’re surrounded by brick buildings with cute shops and quaint restaurants, plus the Beacon Hill Hotel makes you feel like a local. There’s only 13 rooms, so it has a quaint, homey feel.

We ate dinner just a few doors down at Figs, a thin crust pizza bistro that’s equally cozy as it is good. Order the Red Sox pizza and a glass of Octoberfest beer, and you’ll thank us later. Follow that up with a drink on the rooftop (bundle up!) at the Beacon Hill Hotel, and you’ve got the makings for a perfect night in the city!

The next morning we had breakfast at the hotel (get the breakfast sandwich), then ventured out to explore the city!

First stop: Acorn Street

This is Boston’s most photographed street, and it’s steps from the Beacon Hill Hotel. Get there early (like we did) and you’ll bypass the crowds!

Next up, Walk the Freedom Trail!

Now, we didn’t walk the entire Freedom Trail - but we did walk a good portion of it! Take it to Paul Revere’s House and do a self-guided tour inside. It’s well worth the $5 admission to see what life was like back in his day, as Paul Revere himself was an incredibly fascinating guy. (Who oddly really resembles Jack Black!)

Right down the street from Paul Revere’s house is Mike’s Pastry, world famous for their cannolis and decadent baked goods. We had no self control and ordered numerous things - and they were all amazing. Especially the cookies.

We closed out our 18 hour Boston sprint with coffee at George Howell. Not only do they have great branding (something we’re suckers for), but they have fantastic coffee. The baristas are well-trained and serious about what they serve, and the quality proves it. If you go in the fall, be sure to try the Hot Buttered Cider!

MAINE

Just two hours from Boston is Kennebunkport, Maine - our final destination. The drive to Kennebunkport is sprinkled with gorgeous scenery, cute seaside towns, and what seems like an endless amount of lobster shacks. It’s every bit as dreamy as it sounds!

We stopped at Bob’s Clam Hut in Kittery for a lobster roll, fish chowder, and their famous “Fishwhich”. All of which were mouth-wateringly good. If you’re a seafood lover, this is your heaven.

Because of our late start out of Boston, we got there around 2pm and there was no line. From what we hear, lunch can be crazy - so take note!

Next stop was our “home” for the next three nights, the Inn at English Meadows.

This charming B&B completely changed how we view B&B’s (more on that here). It was the perfect blend of cozy and luxurious, and the hospitality and attention to detail that the Innkeeper Elizabeth showed us was unparalleled. We had the “Carriage House Suite” which included a living room, kitchenette, private balcony and walk-in closets. It was like our own private casita - and we can’t imagine staying anywhere else!

We walked to dinner at Old Vines Wine Bar, a welcoming little wine bar that specializes in tapas, wine, and specialty cocktails. Three of our favorite things! If you go, make sure to order the meatballs!

We woke up early the next morning to explore the town of Kennebunkport, and we were so glad we did. We basically had the town to ourselves! We grabbed coffee at Mornings in Paris and Dock Square Coffee House (yolo!) and oo-ed and awe-ed over the picturesque buildings and town square. We enjoyed a delicious breakfast back at our inn, and headed out for a drive!

We were on a mission to find the best fall foilage - and we figured the best way to do so was to explore the old country roads. Sure enough, we were quickly surrounded by colorful trees and farms that looked like they were out of a storybook! We embraced not having a set schedule, and stopped numerous times for photos, leaf frolicking, and...apple picking!

Located on Bridgetown Road, Five Fields Farm is an apple picking dream. They hand you a bag, explain the different varietals, and point you to the fields. The trees are dripping with the juiciest, crunchiest apples we’ve ever had, and picking them was SO much fun. This is a must-do if you’re in Maine in the fall!

We slowly meandered back to Kennebunkport, where we relaxed at our inn before going out for the night. We had drinks at a local favorite, The Pilot House, and then dinner at the newest (and coolest) restaurant in town, The Boathouse. We’re still dreaming about their lobster mac n’ cheese!

Our final day in Kennebunkport was spent exploring. We stopped at Snug Harbor Farm to pet their mini horses and walk around their stunning farm. And then we made our way to Ogunquit, where we walked the famous Marginal Way path along the ocean.

Conveniently, it led us straight to Barnacle Billy’s, where we had the best Lobster Roll of our trip! (Make sure you order the rum punch, too.) We sat along the water and watched the sailboats pass through. The view, the weather, the lobster roll… it all was too good to be true!

The rest of our day was spent shopping in Kennebunkport and enjoying a leisurely happy hour at Stripers Waterside Restaurant. It was the perfect way to close out a perfect (and too short!) trip to New England. We can’t wait to return.

*Do you have a favorite spot that we missed? Leave us a comment and let us know - we’re looking for reasons to return! ;)

Finding Fall with Enterprise

Fall-ing for New England: Boston, MA and Kennebunkport, ME