Fall New England Trip Itinerary

Fall in New England is a magical time of year that feels like it should only exist in a hallmark movie. Last year, Patrick and I planned a ten day road trip traveling through some of the most beautiful places throughout Vermont, New Hampshire, and Maine. I wanted to create a post based on the itinerary we used last fall that will highlight our trip throughout this region of New England. I would highly recommended visiting this part of the country in the fall if you’re able!

Things to Know About Planning a Trip in New England

🍁 The foliage varies year to year, but typically the first two weeks of October are a safe bet on when to plan your trip. I’d recommend using and regularly checking a fall foliage tracker, this surprisingly gives an accurate prediction on when the leaves are expected to change.

🎫 Some areas I’ll mention in this post will require additional reservations (i.e., the Flume Gorge in New Hampshire & entrance fees in Acadia national park). It’s always best to purchase tickets and reservations as soon as possible.

🎃 This region of the country is extremely popular during the fall season, for very good reason! I would recommend booking accommodations as soon as you’re able because things do fill up quickly. Also, keep in mind, this area will be busy and crowded, especially in popular sites and tourist attractions.

📆 Although this is a busy and popular time of year to visit, be sure to look up hours of availability of things you’d like to do as it will vary in the fall season. We learned, a lot of places start to slow down and prepare to close up for the winter by mid October, so be sure you check timing of things. We almost missed a chance to tour a maple syrup farm because we didn’t realize they were closed certain days of the week in the fall!

When To Go

Like I mentioned, it’s hard to recommend a specific time to book and arrange your fall trip since the fall foliage varies each year. However, it seems like the first two weeks of October are pretty consistent and a great time to visit. We also made sure to start our trip in Vermont and end it in Maine since it seemed like the leaves in Vermont were predicted to change sooner.

What To Pack

During the fall, it’s typically cooler temperatures and rainy days so layers are a must! Here’s a basic list to base your packing needs off of:

Rain jacket
Umbrella
Sweaters and cardigans
Layered bottoms (leggings, pants, etc).
Hiking shoes
Beanies and gloves for extra warmth
A warm jacket or a winter coat
Hard warmers (these were amazing to have on the early cold mornings!)
Warm socks

Where to Stay

Throughout most of our road trips, we typically stay at campgrounds because it’s enjoyable and less expensive. For this trip however, it was a little different. We had difficulties finding campgrounds nearby the spots in Vermont we were trying to visit so we only stayed at airbnb’s during that part of our trip. If you’re hoping for convenient locations in each spot, hotels are probably the best option. Keep in mind, because this is a popular time of year for visitors, hotel prices can be expensive and rooms book up quickly. Similarly for airbnb’s, I booked most of ours 6-8 months in advance just to ensure we could find places nearby within our budget.

Some well known hotels in the areas on this itinerary:

Von Trapp Family Lodge (Stowe, VT)
Stone Hill Inn (Stowe, VT)
Woodstock Inn (Woodstock, VT)
Bar Harbor Grand Hotel (Bar Harbor, ME)
The Bayview Hotel (Bar Harbor, ME)

Itinerary Outline

Starting the trip will depend on where you are coming from. Since we were driving from Ohio, we started our trip in Vermont. If you fly in, you can decide which location you’d rather start at (you can’t go wrong either!). Most people seem to fly into either Boston or NYC to start their journey into the New England area. There doesn’t seem to be a convenient airport closer to Vermont or New Hampshire. For this itinerary, I’ll be sharing things to do in the Woodstock and Stowe areas of Vermont, the White Mountains national forest in New Hampshire, and Acadia national park and parts of coastal Maine.

Vermont

We started our trip exploring parts of Vermont. We spent 3 full days here splitting our time between Stowe and Woodstock. After our experience in both, Stowe seemed to have more options for restaurants, activities, and shops compared to Woodstock so keep that in mind! If you’re interested in more details, be sure to check out my Woodstock, VT blog post.

Stowe, VT

Day one

Wake up early to visit cold hollow cider. Take time to explore inside and have breakfast at their cafe.
Take a maple syrup tour at Nebraska Knoll Sugar Farm (tours are free and times vary on the day).
Head back into downtown Stowe and explore shops along main street.
Take a drive through the smuggler’s notch area.
Find dinner in town before heading to airbnb for the night.

🌛Airbnb nearby

Day two

Start the morning with coffee and breakfast at Woodland Baking and Coffee.
Drive over to the Stowe mountain resort to take a gondola ride at mtn mansfield (tickets can be purchased in advance or on site).
Drive by the Von Trapp family lodge and grab a drink at the brewery!
Stop by Stowe maple products to stock up on maple souvenirs.
Have dinner in town.
Stop at original ben and jerry’s for an ice cream before heading back to airbnb.

🌛Airbnb nearby

Day three

Woodstock, VT

Start the day with breakfast at Mon Vert Cafe .
Take time to explore the shops downtown and collect souvenirs
- Yankee bookshop
- Vermont flannel
- Woody’s Mercantile
Walk over to the Woodstock covered bridge.
Walk around the grounds of Woodstock Inn and resort.
Find the iconic pumpkin lined house on Pleasant street.
Grab ice cream at Woodstock Scoops and try a maple cremee!

🌛Airbnb nearby

New Hampshire

Our time in New Hampshire was short and sweet but the fall foliage was incredible! We focused our time here in the White Mountains area exploring the kancamagus highway and the Franconia state park. This was a heavily crowded and congested area so be prepared for lots of wait times.

Day Four

Start drive to New Hampshire (1.5 hour drive from the Woodstock area).
Stop for breakfast on the way at Polly Pancake Parlor (get there early to beat the crowds!).
Drive to Flume Gorge area to hike.
- Reservations required, I recommend booking online in advance for a cheaper price!
Drive parts of the kancamagus highway and stop at pull off spots:
- Hancock Overlook
- Pemigewasset Overlook
- CL Graham Wangan Overlook
- Sugar Hill overlook
- Sabbaday Falls
- Albany covered bridge
Check into campground along kancamagus highway.

🌛Hancock campground

Day Five

Wake up early and head to Artist’s Bluff trail for a morning hike (get there early to beat crowds).
Continue exploring highway and making stops at pull offs.
Drive all the way to Conway, NH along the highway.
Spend downtime relaxing back at camp/accommodations.

🌛Hancock campground

Maine

We took this trip nearly a year ago and I’m still thinking about Maine. It’s truly a magical and dreamy place, that has it all; lakes, ocean, and mountains! This section of our trip was one of my favorites and I cannot wait to return someday. Over the years, Patrick and I have visited several national parks and Acadia is definitely in our top five, it’s such an amazing park. I have a separate blog post with more details about our time in Acadia, you can read here.

Day six

Drive to Acadia national park (4.5 hours from NH).
Take a photo at the national park entrance sign.
Stop by the Hull’s Cove visitor’s center and purchase park pass.
Head into bar harbor to explore the shops and grab dinner.
Head to camp to set up and settle in for the evening.

🌛Blackwoods campground

Day Seven

Watch the sunrise at Cadillac Mountain (timed reservation tickets required, see park’s website for info).
Have breakfast at Cafe This Way.
Stroll around Bar Harbor to collect more souvenirs.
Head into the park and begin first hike at the South Bubble trail .
Drive along the park loop road and stop by ‘Thunder Hole.’
Head back into Bar Harbor for dinner. Some of our favorite restaurants:
- Bar Harbor Lobster Co.
- Side Street Cafe
- Dog and Pony Tavern
- Frenchman Bay Lobster
- Mount Desert Island ice cream
Head back to camp for the night.

🌛Blackwoods campground

Day Eight

Start with an early hike at the Beehive trail (this parking lot + hiking trail get busy fast so arrive early).
Head into Bar Harbor to grab coffee at Acadia Perk.
Drive over to the southwest harbor side of the park and hike the Beech Cliff Ladders trail.
Make a stop at the Bass Harbor Head lighthouse. I’d recommend walking down to the rocks to see the lighthouse from a further angle.
Drive back along the park loop road and spend some time stopping at the ‘Otter Cliff’ lookout.
Head back to camp for dinner and relaxation.

🌛Blackwoods campground

Coastal Maine

This part of the trip, we devoted time to exploring small towns along the coast of Maine. I wish we could’ve had more time here so I’d recommend spending some extra time in these towns if you’re looking for the slow, small town feel. If you’re interested in learning more, check out my coastal Maine blog post here for more details.

Day Nine

Pack up camp and head into Bar Harbor for one last breakfast and time to walk around.
Stop by the Jordan Pond house to try and have an early lunch (I recommend making reservations in advance, we didn’t think to do this so the wait was too long). Be sure to order a popover!
Explore the Jordan Pond path afterwards.
Start driving to Portland, Maine area (3 hr drive).
Stop by Holy Donuts for a sweet treat once you arrive!
Explore downtown Portland and grab lunch or an early dinner at Portland Lobster Co.
Head to Portland head lighthouse for sunset.
Drive to accommodations in Kennebuckport, ME.

🌛 Airbnb in Kennebuckport

Day Ten

Explore downtown Kennebuckport and grab breakfast and coffee at Dock Square Coffee.
Souvenir shop around town.
Take a drive to Ogunquit for the day
- Walk along the marginal way path
- Explore the Perkin’s Cove area
Have one last lobster roll for lunch in town.
Drive over to York, ME and watch the sunset at Nubble lighthouse
- Fun fact: This is where Patrick and I got engaged :)