A Fall Tour Through New England: Charming Towns, Beautiful Homes & Coastal Maine

Visiting New England in the fall has long been on my bucket list. Growing up with the Union Pacific Railroad calendars my mom had on our walls, they always featured rolling hills with iconic barns and churches with steeples. Knowing it gets even better in the fall motivated me to see it in person. So, we packed up our bags and flew here to see what the magic is all about. Let me tell you, it didn’t disappoint.

Our route began in Portland then Vermont, New Hampshire then up to the Belfast and Bar Harbor area of Maine – including Acadia National Park. Here are the details for you and some of my tips if you are looking to see what the fuss is all about.

Tips:

Book your Lodging EARLY – It was quite the laborious process figuring out where we were going to stay even when I was booking in August for my October trip. The prices increase significantly for the leaf-peeping season and the rooms are booked well in advance. A lot of these places even require a two-night minimum stay, which wasn’t our plan as we wanted to keep moving from city to city. Don’t be afraid to stay in the smaller towns – in fact, I would recommend it.

Fly into Portland – take their free shuttle to the hotel for the night (our flight landed around 10 PM).

Take a Lyft (not Uber – our hotel attendant told us Uber charges significantly more) to a

local car rental place downtown rather than the airport – we saved HALF the cost going here rather than the airport.

Take your time – We didn’t have a strict agenda. We did have our hotel/bed and breakfast stays planned ahead of time (a must) so we knew where we were sleeping each night, but don’t be afraid to meander down smaller roads – those, in fact, were some of our highlights, to witness the slow-paced, scenic life was one thing I loved absorbing.

Bring Cash – You’ll need some small bills for the toll roads (we found most of them traveling from Portland to Vermont. The booths operate really quickly with small lines – nothing to stress about. Also, many of these small restaurants and gift shops pass the credit card fee to the consumer by tacking on 3% for credit card usage. If you want to avoid that, bring cash.

Don’t rely on Cell Service to be there – Often you will look down at your phone to see no bars or just one bar. If you have a destination in mind, punch it into your map before you hit the road as you won’t be able to mid-trip in some of these rural areas.

Beautiful views from the Portland Head Light. Located in Cape Elizabeth, the town itself is a charming visit as well.

Use Chat for your guide – I used Chat in helping me find the specific towns I planned to stay in. I told it what I was looking for: foliage, white churches, antiques, covered bridges, etc. It knew well in advance my intentions for the trip and recommended which areas to stay longer and landmarks along the way. It even recommended some good places to eat. It isn’t foolproof as I had it searching for some good apple cider doughtnuts. It took us on wild goose chases leading to places that were closed or even out of business. I would double check some of those unique requests.

Wear Layers - Pack for rain, for cold, for sun, etc. The weather varies considerably each day. So, bring rain jackets, sweatshirts along. We luckily hit it just right and had great weather most of the time. Some recommend even waterproof shoes, but we did just fine without them. I do recommend comfortable shoes -- you never know when you're going to want to take off on a path for a better glimpse. Of course, just check the weather for the time you'll be there.

Check Hours of Operation – As explained using Chat, a lot of these restaurants and shops have odd hours – particularly on Mondays and Tuesdays. I would read about these mouthwatering delicacies only to learn they are closed Monday to Wednesday (the days we were there, of course). This also included the antique stores.

Go Antiquing – There is no shortage of antique stores along your route. We mainly saved the shopping for that in the Maine area, but what we found there was impressive. These stores aren’t like other antiquing I have done – they seem a bit more selective on what they have and less junky than most I have seen. I highly recommend stopping at a few along your way – I think you will like what you see. I grabbed a Maine license plate -- I wish I had snagged a Vermont and New Hampshire one -- I guess there's always next time.

I knew in advance when this train would be coming through on Crawford Notch Road in New Hampshire. It's crossing Sawyer River. The train is the Conway Scenic Railroad -- another way to leaf peep.

Conquering Acadia National Park – One of the best tips we followed the entire trip: Park in Bar Harbor before 8 AM and take the free shuttle to the hikes in Acadia. Know ahead of time which hike you want to do so you know what stop to take. Our bus driver, Tilley I want to say was her name, was a hoot. She gave us a history of the park mixed in with some humor. We went to the Sand Beach stop and hiked the Beehive Loop. Highly recommend this one! Then upon returning, we visited the beautiful beach and hopped back on to the bus to return to Bar Harbor – passing hundreds of cars searching for parking and enduring their long walks to the hikes – by far one of the best tips.

Covered Bridges – Don’t miss them. They are worth it. My favorite one was the first one we had all to ourselves. It was in Warner, New Hampshire and not so well-known. This is where Chat comes in handy – helping you find these hidden gems. I think we hit at least nine of them – and I wish I had time to hit more.

Go Early, Go Early, Go Early – As mentioned with the trip to Acadia, going early to your destination is the theme for the entire trip. We went early to Stowe to capture the iconic church to avoid the crowd. I think crowds in Stowe are inevitable – honestly, we didn’t stay to witness what was in town. But, the crowds were coming. Some even say you'd be fine to skip Stowe. The sunrises are incredible!

About as picturesque as it comes. Stowe, Vermont.

White Churches - As mentioned, Stowe isn't the only place you'll find these charming gems. I love how they pop against the vivid fall leaves. Once again, ask Chat to help you find them in each town.

Fountain Drinks – They aren’t prevalent along your route. So, just be prepared. If you’re like me and come from Utah where there is soda shop on every corner, you won’t be seeing them as much even in gas stations. Restaurants often serve cans or bottled sodas in the Vermont and New Hampshire small towns, at least.

Don’t Forget to Pack These– an extension cord. Many of these hotels won’t have the outlets right by your nightstand. I like to keep my phone charging by my bed. So, if you want it to reach, or to charge other items, you’ll be glad you threw in an extension cord.

Also, include some gum. Those pretty afternoon drives can be calming and tiring. Chewing some gum is a good way to stay alert and awake – especially if you can’t find a McDonald’s for that diet coke.

Eat the Lobster – this is your Maine event. You will be able to find them all over – the shacks or fine dining. You can’t come here and not try it.

Lobster the day we arrived in Belfast, Maine at Dockside Family Restaurant.

Lobster Roll and Macaroni Cheese from Frenchman Bay Lobster Rolls in Bar Harbor

Get Friends’ and Local Recommendations - Some of these places we hit and some we ran out of time, but here are what some friends said to do:

Dee - Portsmouth! Specifically Strawberry Banke - it’s a preserved little village on the coast of the oldest houses in Portsmouth, basically like a walking museum!

Alex - Perkins Cove and Ogunquit were the stars of the show.

Our Innkeeper, Brandon – take the backway into Stowe coming from the Von Trapp lodge – the traffic won’t be as bad.

Smuggler's Notch - Located in the Green Mountains of northern Vermont between Mount Mansfield and the Sterling Range, this road was so scenic and the traditional windy road you imagine it to be. It was worth driving.

One of the many breathtaking views on our hike (The Beehive Loop) at Acadia National Park.

What we didn’t have time to see but will come back for:

Kancamagus Highway – We had this on our itinerary but couldn’t hit it – we even stayed really close to it. It’s widely known and a touristy location, so it might be crowded from what I read this year.

Camden, Maine - We only passed through this charming town, but I want to make it a destination next time.

 Waterbury, VT – we cruised through there, but I want to go back. It looked like a charming, off-the-beaten-path town I want to spend more time in.

Cadillac Mountain - To capture the top of the views in Acadia National Park, they have timed entries only allowing a certain amount of cars through at certain times. You need to check recreation.gov to see how far in advance they allow you to request entry. I believe it's a day or two in advance.

Upstate New York - I think next time we come we might come in on the western New York side. I want to see Lake George. I have been to Schenectady before and would love to see that charming town again -- this time in autumn.

Let's hear what you'd recommend in the comments. Share your experience if you have been so we can all benefit!