New England Fall Travel Guide

New England Fall Travel Guide | Fall Foliage New England | Leaf Peeping | Fall Trip to Vermont | Hiking in New Hampshire in the Fall | Portland Maine Trip | Newport Rhode Island Travel Guide | Mystic Connecticut | Manchester Vermont | Woodstock Vermont

Happy Wednesday, Lovelies!

One of Alex and my favorite fall traditions is taking a fall trip to see some great fall foliage, and spending some time alone! If you’ve been following along for a while now, you know that last year’s trip was to a few different stops in New England. After last year, we were hooked, and still feel like there are so many beautiful places left to visit in New England before we move on to other places.

From the coastline to the mountains, New England has something for everyone year-round, but especially in the fall. Alex and I always try to spend half of our trip in the mountains and the other half by the shore because…fresh seafood!

Just driving through the states of New England in the fall is magical, and should be something everyone adds to their travel bucket list. I am always grateful for time alone with Alex and the beauty that surrounds us on our fall trips.

To make travel planning easy for you, I thought I would share the places in New England that we have visited (so far) and an in-depth travel guide for each place! I hope you find it helpful when planning a fall getaway!

New England Fall Travel Guide:

The places that I will be sharing about today are:

Manchester, Vermont
Woodstock, Vermont
Bretton Woods, New Hampshire
Portland, Maine
Newport, Rhode Island
Mystic, Connecticut

Manchester, Vermont:

Manchester might be our favorite town ever. Alex and I actually have a secret ten-year plan of owning a second home in Manchester because we love it so much. The hiking is incredible, there are so many lakes that are easily accessible that have the prettiest views.

You can rent kayaks at a lot of the (free) state parks to enjoy views from the water.

The town is nestled in the Green Mountains and has everything from delicious eateries to great small shops and even outlet stores that are mixed into the small businesses this lovely town offers.

In 2021 when my daughter was 7 and my son was 4 months old, we took the kids with us and stayed in Manchester for a week and found it was very kid-friendly. We took the gondola up Stratton Mountain and hiked some easy trails, visited the alpaca farm, and of course every pumpkin patch we could find. The kids loved Manchester and my daughter was very upset she couldn’t join us for our fall trip this year.

Where to Stay:

Things To Do:

Drive or hike to the top of Equinox Mountain
Hike or canoe around Emerald Lake
Visit Hildene-the Lincoln family summer home
Visit Orvis or sign up for an Orvis fly fishing lesson
Shaftsbury Alpaca Farm
Mad Tom Orchard for apple picking
Bardwell Farm for cheese
Equinox Nursery and Pumpkin Patch
Outlet Shopping (I love that the outlets are mixed in with the rest of the town and small-town shops).
Gondola Ride and Hiking at Stratton Mountain

Where to Eat:

The Drive from Manchester to Woodstock:

One of my favorite parts of our trip was the gorgeous drive from Manchester to Woodstock, VT along highway VT-100N. We went through so many pretty mountain towns, took in the most breathtaking views, and spent entirely too much time exploring the Vermont Country Store.

Like I’ve said before, the drives are even magical when it comes to fall in New England. Always be sure to take the scenic route if you have the time!

Woodstock, Vermont:

Woodstock is our second favorite town in Vermont, only because it feels so much busier than Manchester. A lot of times in Manchester, you feel like you are the only people there. Woodstock is definitely a bit more crowded but in my opinion, worth the crowd for the scenic views, adorable homes that are perfectly decorated for fall, and the amazing shops/restaurants. One of my favorite things to do in Woodstock is to walk along the side streets and admire the gorgeous homes and their picturesque landscaping.

What To Do:

Visit Sugarbush Farm for Cheese Sampling
Quechee Gorge
FH Gillingham & Sons Vermont Country Store
Billings Farm– a working dairy farm
Middle Covered Bridge
Scenic Drive to Sleepy Hollow Farm
Explore the town’s amazing shops
Marsh-Billings-Rockefeller Historical Park

Where to Eat:

Woodstock, Vermont to Bretton Woods, New Hampshire:

Take the Kancamagus Highway. You won’t regret it. This route takes you through the prettiest fall foliage, small towns, and oftentimes, you feel like you have the whole road to yourself. We have seen wild turkeys, deer, and the most amazing views on this drive. I still have yet to see a moose-but I am determined to one of these days! There are also amazing markets and farm stands along the way you can stop at!

Bretton Woods, New Hampshire:

Bretton Woods is one of our favorite spots to relax and unwind. The White Mountains foliage is so much brighter than any other foliage I’ve ever seen. We love staying at the Omni Mount Washington Hotel because of the amazing views from their historic patio/deck. We also love that once we check into the hotel we don’t have to leave (unless we want to). We love the restaurants at the Omni, the hiking trails right on the resort are amazing, it is nice not to have to think about navigating once we arrive. We do love to explore the surrounding area though, and hiking, even driving on the scenic highways through Crawford and Franconia Notch are some of the most amazing views I have encountered.

Another must you have to add to your New Hampshire bucket list is taking the Skyway Gondola up to the top of the mountain. There is a fun restaurant on top along with tons of hiking trails that aren’t crowded unlike some of the other popular hiking trails people share on Instagram and TikTok.

Where to Stay:

The Omni Mount Washington Hotel
The Lodge at Bretton Woods
Mountain View Grand Resort (Whitfield)

What to Do:

Bretton Woods Skyway Gondola– take a scenic Gondola ride up to the top. From there enjoy food and a beverage at the lodge restaurant, Switchback Grille, or hike the trails at the top.
Franconia National State Park– hike one of the trails or just take a scenic drive through
Mount Washington Auto Road
Mount Washington Cog Railway
The Flume Gorge
Cardigan Mountain Orchard for apple picking
The Basin

Where to Eat:

One of Omni Mount Washington Hotel’s restaurants. We personally love Stickney’s
Harvest Tavern at Mountain View Grand Hotel
The Italian Farmhouse
Six Burner Bistro
Red Fox Bar & Grille

Bretton Woods, New Hampshire to Portland, Maine:

Our longest drive between locations is from Bretton Woods to Portland. It takes about 3.5 hours but we love it. We go through Franconia State Park and once we get closer to the coast, the small towns in Maine are so fun to drive through.

Portland, Maine:

We stayed at the Hilton Garden Inn which we loved because it was centrally located to everything in the city and had great harbor views. When we arrived in Portland and were very hungry so we stopped at Luke’s Lobster for lobster rolls and a beer. We then explored a few lighthouses and the city before eating at Scales! After we ventured out and had a drink at Blythe & Burrows and beer at Allagash Brewery!

We have stayed in Portland several times now and every time we end up having dinner at Scales. It is excellent and I highly recommend it.

Where to Stay:

Hilton Garden Downtown
Portland Harbor Hotel

What to Do:

Visit one of the five local lighthouses
Visit a local brewery
Casco Bay and Cape Elizabeth
Visit Old Port
Eat your way around town

Where to Eat:

Luke’s Lobster-the best lobster rolls you will ever have
Scales– the best calamari and fresh oysters and the best place in town for a whole lobster
Holy Donut– potato donuts that are so incredible. I thought I wasn’t going to like them and I dream about them at night now! haha!

Where to Drink:

Allagash Brewing Company– Try their white beer it’s amazing and was our favorite of all the beers we tried in Portland.
Blythe & Burrows– sit at the front bar for a fancy martini or go through the secret bookcase to the basement bar for a fun speakeasy vibe
Independent Ice Co. – another really cool bar with a great outdoor patio that specializes in Whiskey and whiskey-based drinks. I am not a huge whiskey fan and they made their drinks with vodka for me so don’t let the whiskey part deter you, this spot is really neat!

Pitstop in Kennebunkport:

On our way to Newport, we stopped in Cape Elizabeth to explore the Portland lighthouse and ventured over to the cutest coastal town of Kennebunkport, and grabbed some great “clean” chowder and lobster rolls at the Cape Pier Chowder House.

Newport, Rhode Island:

I thought the homes (mansions) in Palm Beach, Florida were unreal until I had the opportunity to drive on Ocean Avenue and see the lavish mansions that most owners deem as their “summer cottages” in Newport, Rhode Island.

We stayed at Hotel Viking and loved that we could bike around town. We were also welcomed with complimentary margaritas upon checking in. They have a great rooftop bar with small bites and a closed-in patio with an outdoor fireplace.

We drove along Ocean Avenue exploring the cliffside mansions and walked around town to do some shopping. For dinner, we ate at The Mooring and had the best raw oysters and pumpkin spice mules! The next morning, we walked along the Cliffwalk to take in the views and explore the historic mansions from the outside.

Where to Stay:

What to Do:

The Cliffwalk
Drive along Ocean Avenue for views of the mansions along the coastline
International Tennis Hall of Fame
Shop along Bowen’s Warf or Thames Street
Visit one of the lighthouses
Gooseberry & Easton’s Beach

Where to Eat:

The Mooring Seafood Kitchen & Bar (we had the best raw oysters and Pumpkin Spice Mules here)
Bouchard Inn & Restaurant
Rooftop Bar at Hotel Viking

Mystic, Connecticut:

I love this river town. They have the greatest restaurants like S&P Oyster and Red 36, and you can’t leave without grabbing a slice of iconic Mystic Pizza!

The town itself has great shopping and I love walking around the marina and admiring all the beautiful boats.

What I Wore:

What is a fall trip without some fun fall fashion!? If you are planning on taking a trip to New England in the fall be sure to pack for ALL THE ELEMENTS we went from 45-degree days to 75 and sunny depending on our location!