"I recently went on a road trip with my mom to several New England destinations. It was a uniquely special getaway in that not only did we make tons of new memories together, but we got to explore a handful of cities that neither of us had visited before. Growing up in California didn’t necessarily warrant lots of East Coast trips, but after living in New York post-college, I naturally got more and more curious about this (undiscovered by me) side of the country.
New England as a whole is a charming and highly historical area, but it also boasts so many different experiences within a somewhat small corner of the U.S. It’s a practical and fulfilling place to visit because you can realistically pack a lot into just one trip. If you’re interested in planning your own getaway, I’m sharing some tips on putting together a well-rounded New England fall itinerary. Below, you’ll find my personal suggestions on where to go, eat, and stay since I know firsthand that it can be hard to narrow down your list to just a handful of choices. All you have left to do is book your airline ticket, rental car, and accommodations—then go explore all that New England has to offer in the fall.
The Best Time to Visit New England
Unless you love braving harsh winter conditions, you’ll likely agree that planning a New England trip in the middle of the cold season isn’t ideal. Spring can also be iffy because of the moody weather, and summer is peak season (which means you’ll have to spend a pretty penny to travel and stay in the area). This leaves one season that I’d argue is prime time to visit New England: fall.
A fall getaway is a dreamy experience in and of itself, but getting to immerse yourself in the magic of an East Coast autumn is truly special. This side of the country boasts stunning fall foliage, cool yet comfortable temps, and cozy towns that are filled with charm. Plus, after the hectic summer season, fall brings more affordable rates on both airfare and hotels.
How to Plan Your Itinerary
1. Book early
As is the case with most travel, it’s best to plan your trip as far in advance as possible. Choose your ideal travel dates and then check some alternatives to see if there are any noteworthy price differences. I love checking the Hopper app to confirm the best time to book flights, but as far as hotels go, book as early as you can (things tend to fill up quickly!).
2. Include a mix of hot spots and lesser-known small towns
The exact cities my mom and I visited are listed below, and I’m so glad we hit some lesser-known towns mixed with more “touristy” locations. This is a good game plan that ensures your trip is well-rounded with popular destinations as well as more unique spots with a local feel. I’ll be carrying this strategy through all my future travels!
3. Account for 1-3 nights at each spot
Figuring out how much time to spend in a particular city is perhaps the hardest part of trip planning. You want to allow yourself enough time to enjoy each place, but you also don’t want to feel bored or like you could have checked out earlier. In my experience, a good strategy is to map out your exact activities, including any meal reservations, sightseeing excursions, or shopping you want to do. By starting with the specifics, you should easily be able to tell whether you need one, two, or three nights in each city.
4. Fly into one airport and out of another
Because my mom and I made a road trip out of our visit, we thought the most logical way to go about it was to fly into our starting city and out of our final stop. Keep in mind that if you’re following this method, you’ll likely have to spend a bit more on a rental car (most rental car companies charge extra for using different pickup and dropoff locations). With that said, this strategy was much appreciated at the end of our trip, when we were both tired and ready to get home. Having to drive back to where we started from would have been somewhat of a pain.
5. Make reservations at a variety of restaurants
No New England trip would be complete without ample seafood, but you can only eat so many lobster rolls before feeling burnt out. To avoid maxing out on your palette for fish, make sure you book reservations at a variety of restaurants that offer different cuisines. I learned that while the East Coast might make an insanely good bowl of clam chowder, they also have great Italian, Mexican, and American food. Variety is key!
My New England Fall Itinerary
Not sure where to go? To help you plan the specifics of your New England fall trip, I’m sharing our exact itinerary below. All of these cities are easy to get to once you arrive on the East Coast (the longest car ride we took was only three-and-a-half hours!). For reference, we flew into Providence, Rhode Island, and out of Portland, Maine.
1. Watch Hill, Rhode Island
Length of stay: Day trip
Take a day trip or spend a night in the less-frequented but stunning town of Watch Hill, Rhode Island. If this seaside spot sounds familiar to you, it might be because Taylor Swift owns a mansion here. While you (sadly) won’t have an invite to Taylor’s house, you can walk right alongside her place to scope out all the swoon-worthy properties that line the coast.
The town is super walkable and flaunts tons of local boutiques, restaurants, and coffee shops that you can easily spend a day exploring. Finish things off at the iconic Ocean House hotel, which is very high-end and luxurious yet allows non-guests to enjoy cocktails and a meal on the veranda.
Where to stay: Staying in Watch Hill is quite pricey, and the hotel options are limited, so I’d recommend spending just the day there before driving to Newport for the night.
2. Newport, Rhode Island
Length of stay: 2-3 nights
This was the destination that surprised me the most during our trip. I thought it would have a much “bigger city” feel to it, but I was pleased to see that much of the town had historical charm and a cozy, nautical vibe. The locals were extremely friendly, and there were so many good restaurants. While in Newport, you must eat at Pasta Beach (amazing pizza), Bar ‘Cino (delicious sandwiches and superior service), and Belle’s (a stunning brunch spot on the water).
As far as activities go, don’t miss out on wine tasting! My mom and I had such a special experience at Newport Vineyards. The property was stunning, and they offer a full restaurant and a variety of tasting options. Plus, if you book a room at The Pell (more on that below), it’s a very quick drive or Uber ride away. Other must-dos in the area: walk around the historic Point neighborhood, get coffee and pastries at Sweet Berry Farm, and have waterfront cocktails at the Castle Hill Inn.
Where to stay: Both The Pell and Wayfinder Newport are affordable yet comfy accommodations. Both properties were recently renovated and are centrally located without making you feel like you’re stuck in the busiest parts of town. Newport can be quite a splurge, but these choices are well-priced, immaculate, and convenient.
3. Kennebunkport, Maine
Length of stay: 1-2 nights
Known for its stellar beaches, scenic lighthouses, and slow lifestyle, Kennebunkport is the kind of place you’ll want to visit repeatedly once you experience its charm. Just driving through the area makes you feel like you’ve taken a step back from the stress of day-to-day life. Similar to Watch Hill, you could spend the good part of a day just walking around the neighborhoods and admiring all the New England-style mansions. In town, window shop the various boutiques and gift shops, then spend happy hour at Ocean Restaurant, The Burleigh, or Via Sophia—all three are great for a girls’ night!
Where to stay: If you’re looking for a truly authentic Kennebunkport experience, The Cottages at Cabot Cove will deliver just that. With only 16 cottages on the grounds, your stay will feel ultra-private, quiet, and local. No details are missed, and each cottage is outfitted with nautical-inspired decor (very Nancy Meyers-esque). Breakfast is delivered to your doorstep each morning, and rates are reasonable considering how expensive staying in this area can be!
4. Portland, Maine
Length of stay: 1-2 nights
I’m sure it’s less of a surprise that Portland, Maine, made this list, but it’s a practical and cute place to end a New England getaway. If you like harbor cities and are interested in museums or boat tours, this is the place to conclude your travels. The Portland Museum of Art is a popular sightseeing spot, and I’ve heard many people rave about the Wine Sail excursions. When it comes to dining, don’t skip Via Vecchia for Italian bites and Scales for the best lobster roll in town. Before your dinner reservations, stroll around the cobblestone streets or alongside the harbor to take in true Portland culture.
Where to stay: The Lincoln Hotel is reason enough to visit New England. The boutique property is located inside a reimagined textile mill and flaunts an inviting yet historical feel. There’s a coffee shop, restaurant, and two bars inside the hotel, and it’s located in a quaint town just outside of Portland. This property would make a great home base if you plan on visiting Kennebunkport and Portland since it’s located right between the two cities. Plus, you’ll love the high-ceiling loft layout, cozy fireplaces, and brick detailing in each guest room.
Kara Thompson, Contributing Home Writer
Kara Thompson is a Denver-based journalist with a bachelor’s in journalism from the University of Oregon. In 2022, she left her full-time job as an editor and started her own writing, editing, and social media firm, Kara Thompson and Co. She has over five years of experience writing lifestyle content for publications including townandcountrymag.com, elledecor.com, goodhousekeeping.com, and Parents, where she covered all things home, food, health, travel, fashion, and holidays.