New England: A Road Trip for Leaf Peepers & Beer Drinkers
Autumn has always been my favorite season and visiting New England in the fall has been a dream of mine for as long as I can remember. Last October, I finally made it reality…and it did NOT disappoint! I created this road trip itinerary to wind through six different states over six days. And with the flexibility of having a car, you control the pace.
Welcome to New England: A Road Trip for Leaf Peepers and Beer Drinkers! This itinerary was created for those who dream of beautiful hikes surrounded by fall foliage, love local beer, enjoy seafood, and seek a little bit of luxury.
Travel Tips
Road trips are great because you have so much flexibility in your itinerary. However, you also want to make sure you allot plenty of time to actually enjoy your stops. To keep yourself from spending the majority of your trip in the car, try to plan for less than 4 hours in the car a day.
This itinerary is built to provide a 6 day guide, but days of the week are not determined for you. Make sure you always check the hours of operation for every stop you’re interested in, as many small businesses are not open every day. (And I always try to prioritize small, local businesses in my itineraries!) Additionally, this itinerary was created pre-COVID, so check for any restrictions that might currently exist.
Newport was the vacation spot for many of the elites during the American Gilded Age. The mansions that were built there are quite spectacular. While this itinerary includes a tour of Vanderbilt property the Breakers, you have a few to choose from if you’d like to schedule a tour. These homes definitely redefine opulence.
This scenic drive is one of the most famous autumn drives in the world. Which means…weekends in the fall bring serious crowds. If you’re able to go during the week, you’ll be dealing with far fewer cars.
If a weekday isn’t possible, go as early as possible! I find most hiking trails don’t get busy until about 10:00am. If you can plan for an 8:00 start (or earlier!)…you’ll find you have the park almost to yourself. Well, for at least a couple hours 😉
It’s no secret that New England beer is my favorite beer. I’ve provided a ton of local breweries on this itinerary, but there are SO. MANY. MORE. Make sure you stop in one (or two or three…) shops where you can peruse local beer selections. You’ll find a beer cornucopia just waiting for you…
Day-to-Day
DAY ONE: Saratoga Springs, NY to Lenox, MA
This itinerary begins with an afternoon arrival in Saratoga Springs, New York. Start with lunch at Druther’s Brewing Company. They have a great food menu in addition to their microbrews and also have a beautiful patio if the weather is nice.
After you finish lunch, take some time to wander around the cute downtown area of Saratoga Springs. There are great shops and plenty to browse! Stop in Saratoga Coffee Traders if you need a quick pick me up. We also popped into Putnam Wine, where we perused wine from around the world and bought a couple bottles to enjoy during our trip.
Head over to Saratoga National Historic Park by mid-afternoon. Not only will you see the site of a famous Revolutionary battle, but the views in the fall are beautiful. Stop by the visitor center to get a map and embark on your own self-guided tour of the park.
It will take you about 1.25 hours of driving to reach tonight’s stay in Richmond, Massachusetts. You’re heading for your first night of luxury on this trip, The Inn at Kenmore Hall. When you arrive at the property, you’ll be invited to help yourself to their fully stocked bar cart and provided with some delicious chocolates from a local company in the Berkshires.
You can read my full review of this property here.
For dinner, head into nearby Lenox. This lovely small town has an abundance of restaurants to choose from with multiple varieties of cuisine. We opted for Brava, a wine bar with great tapas. Another option would be Nudel, specializing in a seasonal menu that changes nightly. Reservations for Nudel are strongly recommended.
DAY TWO: New Haven, CT to Newport, RI
Wake up and enjoy a delicious cooked-to-order breakfast, included at the Inn. Take some time this morning to explore the grounds of the Inn, where you’ll discover peaceful nature trails and enjoy beautiful views of the Berkshires. Alternatively, you could hop back over to Lenox and wander through some of the small shops.
Whatever you choose to do, keep in mind that it will take you 2 hours to drive to your next stop, New Haven, Connecticut. Plan your arrival for lunchtime, where you’ll grab a burger at Louis’ Lunch.
Why is this the decided lunch stop, you might ask? Well, this establishment claims to have invented the hamburger and continues to churn out the original recipe on a daily basis. Don’t expect anything fancy, just good quality meat, tomatoes, onions, and cheese squeezed between two pieces of toasted bread. I also recommend the potato salad!
Order at the counter and grab a table if there are any available. Or take your order to go and have a little picnic in nearby New Haven Green.
Once you’ve finished lunch, head over to the Yale University Visitor Center to pick up a map for your self-guided tour of this beautiful 300-year-old university campus. That’s right, this historic Ivy League university is older than the United States itself. Take some time to appreciate the inviting green spaces and the impressive architecture of the buildings that sprawl across New Haven. Don’t miss the Beinecke Rare Book and Manuscript Library which holds one of the rare copies of the Gutenberg Bible. Yale’s copy was printed around 1455 and is an awe-inspiring testament to human history.
Now that you’ve been sufficiently awed by this impressive institution of higher learning, hop back in the car and make your way to Newport, Rhode Island. Plan to take about 1.5 hours for this leg of the drive. Before you cross the bridge to Newport, make a stop at Sons of Liberty Spirits Co. and try out a flight of craft whisky. From there, pop over to nearby Whalers Brewing Company and try a flight of beer. Enjoy this space as Whalers is one of the most beautiful breweries I’ve ever had the pleasure of visiting!
After you’ve finished your sampling (and maybe made some purchases to take along with you!), finish the journey to Newport. Check-in to your next stay at the Cliffside Inn, an elegant B&B in an 1876 mansion with views of the water. Enjoy their welcome reception with complimentary wine and cheeses after you’ve settled into your room.
For dinner, you have a host of options in downtown Newport. And you are now officially dining on the New England coast! If you’re a seafood lover, now is definitely the time to indulge. Tonight, feast on stuffies (Rhode Island-style stuffed clams), lobster, and fresh oysters.
DAY THREE: Newport, Cape Cod, Plymouth, & Boston, MA
Wake up and enjoy your provided breakfast at the Inn. After you’re finished, head over to the Cliff Walk, which is conveniently located right down the street from Cliffside. This National Recreation Trail hugs the curves of the cliffs overlooking the Easton Bay and onwards to the Atlantic Ocean. Though we were met with gale force winds and the spray from strong ocean waves during our visit, it didn’t stop us from enjoying the incredible beauty and admiring the power of the water. I was, however, very happy we brought our rain gear! Walk down the 40 Steps to get up close and personal with the Bay.
You’ll notice the Cliff Walk meanders by a plethora of Gilded Age era mansions. Newport holds many of the summer residences of Manhattan’s wealthy and elite, built in the late 1800s. These homes redefine opulence, with each family (in the tradition of “keeping up with the Joneses”) trying to outdo their neighbors in displays of wealth and class. While there are many to choose from, we decided to tour The Breakers, one of the many homes of the Vanderbilts, of the railroad tycoon variety.
I’ve been to palaces around the world, and I’m not sure any of them compared to this extravagant and garish display of wealth in the age of American “royalty”…
When you’ve had your fill of Lives of the Rich and Famous, it’s time to get back on the road. Give yourself about an hour and a half to drive over to the Cape Cod area, where you can stop for some refreshments at Naukabout Brewery. This is also a great time to grab lunch. You can opt to continue on down the Cape to find lunch, or, like us, you can choose to make a quick stop at nearby Cooke’s Seafood, a Cape Cod family favorite for over 35 years.
Your final destination tonight is Boston, which is a little over an hour from Cooke’s. Along the way, make a quick pitstop in Plymouth, MA, where you can see not only the famous rock of the same name, but also a memorial to those first settlers from the Mayflower in 1620.
Head to your hotel to check in once you reach Boston. There are countless places to choose in this city, from luxury hotels to comfortable Airbnbs. We opted for a Hilton hotel downtown, as I had a free night certificate (thanks to the rewards from one of the credit cards I carry!). Settle in to your hotel and wander the city on foot. Boston is a beautiful, historic city, and there’s so much to enjoy. It’s definitely a city for wandering and getting lost in.
Head over to Bow Market, where you’ll find some unique local shopping as well as the incredible Rebel Rebel wine bar and Remnant Brewing. Enjoy some drinks before you walk over to Field & Vine for dinner, a gorgeous restaurant focused on seasonal, farm fresh menus with a focus on small plates. Reservations recommended.
DAY FOUR: Boston to Conway, NH
If the weather is nice, this would be a great morning to explore some of the 2.5 mile Freedom Trail that meanders through downtown Boston, bringing you to some of the most famous sites of the American Revolutionary War. There are 16 sites in total, so check out the Freedom Trail website to plan your route.
Leave Boston by late morning for your next stop: Conway, New Hampshire. It will take you about 2.5 hours to reach Conway, but the drive is beautiful. You’ll be awarded with some gorgeous fall foliage, especially as you approach White Mountain National Forest, your destination for tonight and tomorrow.
When you arrive in Conway, stop at Tuckerman Brewing Company for some local brews and lunch. A full menu of food is on offer from Thursday to Saturday.
Conway is a small town, so there aren’t an abundance of hotels on offer. We opted to stay in an Airbnb, which was comfortable and suited our needs for a night. The biggest reason you’re going to want to stay in Conway tonight is because it marks one end of the Kancamagus Highway, where you will be adventuring early tomorrow…
If you are staying in an Airbnb, check out Veno’s Specialty Food & Meats and purchase some items to prepare on your own for dinner. They also have a great beer selection, so go ahead and pick up some different local beers to pair with your dinner tonight.
Get to bed early, tomorrow you start your day before the sun!
DAY FIVE: Kancamagus Highway to Stowe, VT
Today is the leaf peeping day you’ve been waiting for! You’re in the heart of New England fall foliage: driving the 34.5 mile Kancamagus Highway from Conway to Lincoln. The Kanc, as it’s affectionately called, weaves through White Mountain National Forest, providing one breathtaking view after another.
Kick your day off as early as you can. Ideally, you want to be leaving for your drive as soon as the sun is out. This is one of the best fall foliage viewing areas in the entire country…so expect it to be crowded! Luckily, you can beat the crowds just by getting an early start.
There are many great hiking trails to choose from on this stretch of road, of varying difficulty. We opted for the approximately 3-mile Boulder Loop trail. At its highest elevation, you’ve got a 1000-ft vantage point over the incredible Passaconaway Valley.
In addition to hikes, you will also come across various points along the highway where you can easily stop and enjoy some scenic views. From picturesque covered bridges, to the clear water of the Swift River, hugging the highway, everything will be surrounded by that beautiful foliage you’ve come here to enjoy. The Lower Falls scenic spot is an excellent place to stop to snap some gorgeous photos right off the highway.
Take your time and as many stops as you can squeeze in. Soak up as much of the natural beauty as possible this morning.
As you reach the end of the scenic highway, you’ll approach Lincoln, NH. Stop for lunch and — you guessed it! — some brews from Woodstock Inn Brewery.
By early-afternoon, you’ll be back on the road, making the 2-hour drive to Stowe, Vermont. If it happens to be Sunday, don’t miss a stop at the WhistlePig Tasting Room. WhistlePig produces some delicious rye, and if you’re a whisky enthusiast, you are definitely going to want to enjoy some samples.
If you’re needing a bit of a pick-me-up (you did wake up quite early today!), stop in Vermont Artisan Coffee and Tea for a hit of caffeine and maybe a baked treat, conveniently located in the same building as WhistlePig.
After refreshments, it’s time to check-in to one of the best Airbnb stays of your life. Take the private stairway on the side of the house, leading you to your apartment. The view that greets you from your deck is magic. Trust me…you’ll want to pinch yourself right about now.
Click here to view the full listing and book this incredible stay.
Sit on the balcony for as long as you want. I can confirm, it’s very hard to tear yourself away from that view. After you’ve watched the golden hour magic play out across the trees and mountains, make your way into downtown Stowe for dinner. This charming town has an abundance of shops and restaurants to choose from. If you’re in the mood for another great wine bar, I suggest getting dinner at Cork. They have an extensive wine and beer selection, delicious charcuterie boards, and a small retail shop where you can purchase items and drinks.
After dinner, head back to the Airbnb. Hopefully you brought your swimsuit…now’s the time to wind down in the on-site hot tub with a glass of wine or one of those New England beers you’ve picked up along your travels.
DAY SIX: Stowe, VT
Enjoy breakfast at your Airbnb, overlooking the mountains, or head into Stowe and choose from one of the many cafes. After breakfast, allow yourself to wander, ramble, and roam in this darling town. Stowe is one of my favorite New England towns, and I love discovering new shops, restaurants, and views with each visit.
Today is your final day to round out your rapidly growing beer collection from this trip. Try a flight at Idletyme Brewing Company before heading to one of the region’s most famous breweries. The Alchemist put the New England style of beer on the map, and it sells out almost daily. You can sample on site, but make sure you get in line early to purchase your cans to go. Heady Topper is one of the most well known, but every beer I’ve ever purchased from the Alchemist has always been amazing. Once you’ve made your purchases, head to von Trapp Brewery and Bierhall for one more flight. This hall is huge, with a large retail shop.
This itinerary is winding down…but you’ve got two more stops. From von Trapp, head south to make a quick stop at Cold Hollow Cider Mill. If you can make it with apples, you’ll find it at the Mill. And is it even fall in New England without a fresh apple cider donut paired with hot apple cider? Answer: No. It isn’t. These donuts also freeze and reheat incredibly well, if you want to take some home to enjoy after your travels.
For lunch, make a stop at Prohibition Pig for excellent BBQ paired with beer brewed in their colocated brewery.
If you have a little extra time, one additional activity you can tack on to your day in Stowe is to take a gondola ride from Stowe Mountain Resort. You’ll get more spectacular views of the town, surrounding area, and Mt. Mansfield.
Head home knowing you’ve just ate, drank, and leaf peeped your way through some of the best New England has to offer. However, you do have one more task to complete when you get home… Compare your haul to mine! How did you do??
