Let’s chat about our first family trip to Maine!

Last week, Dave, Brady and I went on a four-night adventure to Maine. I’d been to Maine twice before with Dave, we were engaged there (on Peaks Island), and Dave grew up there too. Maine is very special to us, and we’ve wanted to go there with Brady for quite some time.

Portland, Maine is just a short direct flight from Charlotte, and we left on a Tuesday morning and came home on a Saturday night. (Whenever possible, we really try to return from trips on Saturdays instead of Sundays, so we have a whole day to get organized before the week kicks in. But I ended up having to teach a class on Sunday morning anyhow, after we got home late due to some airport delays, but no big deal). Overall, we loved our Maine trip, and I’d definitely recommend it as a family (or couples) trip. It’s pretty affordable too.

• We did two nights in Portland, and you can check out my video on Portland/Freeport here.
• We did two nights in Bar Harbor, and you can check out my video on Bar Harbor here.

Our first family trip to Maine: Highlights from visiting Portland, Freeport and Bar Harbor

Let’s get to the family trip to Maine highlights …

Portland

Visiting the Lobster Shack at Two Lights and Portland Headlight and spending time with Dave’s family

Brady was so excited to see his cousins in Maine, and it was an adorable reunion. Pretty much as soon as we got off the plane and picked up our rental car, we were off to meet up with two of Dave’s sisters, their spouses and two of Brady’s cousins.

We met at Lobster Shack at Two Lights, a super-casual restaurant with an incredible view. Dave and I had been to Lobster Shack once before, and it’s a meal worth remembering. This is one of those places that’s been featured on food shows — not only because of the fresh seafood, but also because of the setting.

After we enjoyed some buttery and delicious lobster rolls at a bright red picnic bench, we walked along the rocky coast catching up with family. It was a little bit cloudy this day, but the view was still spectacular. If you ever go to Portland, Maine, Lobster Shack in Cape Elizabeth totally needs to be on your must-visit list. You don’t need a reservation, you just show up and take it all in.

(Here are my sunglasses.)

On this day, we also visited Portland Head Light in Cape Elizabeth, which is another public park on the gorgeous Maine coast. The focal point of this park is the Portland Head Light lighthouse, but there’s also a ton of green space, walking trails and coastal views, as part of Fort Williams Park. Dave and I had also been to this spot on a previous trip, and it was just as beautiful my second time seeing it. 

Walking to Hadlock Field to see the Portland Sea Dogs play and win a baseball game

I’ve mentioned before that Brady is Mr. Sports right now. Well, he hasn’t been on a baseball team, but he loves to play baseball at home, and we recently took him to his first minor league baseball game in Uptown Charlotte. He was very pleased to know we had a sporting event on the agenda during our family trip to Maine.

On our first night in Portland, we went with Dave’s family to see the Portland Sea Dogs play at Hadlock Field in downtown Portland. We could walk there from our hotel, which was fun too. I do miss walking the city like I used to do in my San Francisco days, and it’s nice to revisit it as a tourist in other big(ish) cities every once in a while.

(Here are my sneakers.)

At the game that night, Brady got to meet the Portland Sea Dog mascot, watch some baseball, hang with his cousins and eat a famous Sea Biscuit ice cream sandwich. This was a casual sports-filled night, and it was a perfect way to kick off our trip.

The Sea Dogs won that night too, which made it even more of a good time. But the best part was definitely the family time with the big group that we sat with. (We all had pretty inexpensive tickets in different areas of the stadium, but we were lucky enough that there were some open seats together, so we all sat in a line, hanging out and chatting it up.)

Freeport

Checking out where Dave grew up, visiting his schools, his childhood house and even old jobs (and shopping at the home of LL Bean)

Dave grew up in Freeport, Maine, which is a very small town about 25 minutes from Portland. We spent much of the day there on our second day, and it was a very chill day.

We took Brady to play on the playground of Dave’s elementary school (and we played too), we went by Dave’s middle school, and we even checked out the new football field at Dave’s high school (they didn’t have football back when he was there).

The weather was so beautifully mild and sunny this day, and it was great to have these moments outside. Freeport is nothing like Charlotte, and I like for Brady to see different places like this — the homes are more spread out, the neighborhoods are less defined and the small-town charm is certainly there.

That day we also went to lunch at Gritty’s Freeport Brew Pub and met up with a couple of Dave’s childhood friends who still live in Freeport. Dave used to work at Gritty’s, and he’d taken me there once before. 

After lunch, we went to the Freeport outlets and the home of the original LL Bean store too. The LL Bean store is actually a set of stores on a sprawling campus, and they’re really fun to look through. I bought this sweater and ended up wearing it the very next day. 

We had promised Brady we could get him new sneakers for his upcoming school year on this trip, so we also got him those as well as a couple outfits at the Under Armor outlet, so it was a productive day. 

(Here’s my dress.)

I really enjoyed going back to Freeport! It’s so very different from where we live and it felt like a breath of fresh air. The little stores and restaurants in the (very small) downtown are quaint and welcoming, and it’s all extra special to us because it’s where Dave grew up. We let Dave narrate much of our car rides through Freeport, and that was my favorite part of being there.

Bar Harbor

Cruising around Frenchman Bay on the Schooner Margaret Todd and soaking up the beauty of Bar Harbor 

Friend, when we arrived to Bar Harbor on the most bluebird of a day, it literally took my breath away. I had no idea Bar Harbor would be so incredibly gorgeous, and it was hard to imagine that during the three-hour drive up from Portland.

We loved our first day in Bar Harbor so much, and it was perfect. We also loved walking around little downtown Bar Harbor and enjoying some great food — Terrace Grill was a highlight because of the fresh food and the amazing coastal view. (As well as taking the free bus for tourists, which was so convenient.)

My favorite, favorite thing we did this whole trip was go on the Schooner Margaret Todd via Downeast Windjammer Cruises. We were supposed to go on a sunset cruise on our final night, but that cruise was cancelled due to pending weather. So we switched to an afternoon cruise on the day we arrived in Bar Harbor, and we loved it. We got to see the islands of Maine, look for porpoises in the bay and soak up the ocean breeze, while the most-captainest-of-captains shared insight and clock-directions of landmarks. (For example, “Porpoise, 2 o’clock.”)

(Here’s my sweater.)

When we first got on the schooner, they asked if anyone wanted to volunteer to help hoist the sails, and I jumped at the chance. And this activity was not just for show, it was actually a lot of work. Two other volunteers and I helped one of the crew members pull up a sail, and we really did need to pull hard. Good times!

(Here are my sandals.)

Once the cruise was over, we walked down to the rocky beach and soaked up the views. Once again, Bar Harbor is breathtaking! And I’m so glad we had this great day, because the next day felt quite opposite. More on that next …

Making the best of terrible weather and walking around Cadillac Mountain in ponchos

When we were packing up for our trip, the weather for all the days we’d be there looked perfect. Then, all of a sudden on the day we left Charlotte, it started to look like a tropical storm would be making its way up on our last full day in Maine. There was nothing we could do about it, so we just had to try and have fun in the rain. And I would say — mostly — we did have fun in the rain. We even swam in our hotel’s indoor pool and used the hot tub and steam room, which were all a nice surprise we didn’t even know were available until we realized we needed indoor activities on that one, full, rainy day.

Anywho, back to the national park … We had been looking forward to hiking around Acadia National Park for a long time, having read all about it in a book about Maine. And while we gave it a shot, it was pretty miserable in the cold rain. We bought $3 ponchos from the gift store on top of Cadillac Mountain (and we ended up using those ponchos all day, so that was $9 well spent) and attempted to stroll along a trail. But we kept stepping in puddles and being blown around from all directions — so that adventure didn’t last long. So we shivered our way back into our rental car and headed back to the hotel.

By the way, you have to make a reservation and pay a fee to drive up Cadillac Mountain, and had it been a clear day, we would have been able to see the coast and nearly all of Maine. But, it was very dark and cloudy, so our visibility was minimal.

(Here’s my hat, here are my shorts, here’s my sweatshirt and here are my shoes.)

Even though our trip to this national park was not what we expected, it will be memorable. Brady sang a little tune as we were out walking the rocks in the rain about being “here, in a trash bag” (referring to his poncho and sung to the tune of a song from “The Polar Express” movie), and we keep singing it over and over again now that we’re back home. Sometimes things don’t work out perfectly, but you still end up remembering them well. That’s life!

Other favorites from our first family trip to Maine …

In Portland, we stayed at The Westin Portland Harborview, and it was a no-frills hotel in a decent location. We liked that there was a coffee shop in the lobby, and we were only a 10-minute walk from the Old Port neighborhood for dinners out. Our room was small, but it got the job done. And we always try to stay at Marriott properties to earn points and use the app for checking out, and this was one.

In Portland, we loved walking around the Old Port neighborhood in the evening. I would recommend making a dinner reservation ahead of time, because we had a hard time finding a place that would take a walk-in, but we ended up loving our meal. We also loved these evening pictures near the water (so helpful that Brady can take our photos now) …

In Bar Harbor, we wanted to stay at the Bar Harbor Inn, but it had a three-night minimum, so we ended up at the Bluenose Inn. The Bluenose Inn was a funny place. The decor in the rooms and common areas was so incredibly outdated, but it had some major charm. Like I said before, we found the indoor pool, hot tub and steam room and loved that amenity. And the best part is that the hotel offered live piano music in a floral-couched lounge nightly, and we made it back to watch that the two nights we were there. Also, our hotel room had a lovely little balcony, so we could hang out there after Brady went to sleep. If we ever go back to Bar Harbor, we’ll probably try to stay at the Bar Harbor Inn, but the Bluenose Inn provided some entertainment for sure.

In Bar Harbor, we had some good food, and my favorite meal was at Terrace Grill at Bar Harbor Inn. But Brady would say that Geddy’s was his favorite, because they had a lot of great variety in their kids’ menu, and his meal was served on a frisbee he got to keep. We did need a reservation for Geddy’s and made it the morning of our final day. 

In Bar Harbor, we had one dinner seated near a window on the main downtown street, and this was a great place to people watch. Overall, Bar Harbor (and Portland and Freeport for that matter) are super casual. Everyone is in comfy clothes and walking shoes and lots of layers, because it was warm in the day and chilly at night. Also in Bar Harbor, as mentioned, there’s a free local bus that takes tourists from nearby hotels to the main downtown stop. We loved that perk.

Closing thoughts on our first family trip to Maine

When I told people that we were heading to Maine for a family trip, I got a lot of confused stares. Why visit Maine? Well, Maine is a beautiful state! While I’ve only been in a handful of cities along the coast in Maine, I can attest that there are many gorgeous things to see and do there. There’s no real hustle and bustle. It’s chill. And it’s casual.

(Here’s my purse.)

We liked that Portland was easy to access with a direct flight, and we were able to be near the ocean too. Brady had a blast seeing his cousins, we loved catching up with family, and we spent a lot of quality time in our small family unit too. I wish we had stayed maybe one extra night — but as Dave says, it’s better to leave a vacation wanting more than to wish you had headed home sooner. I agree. 

We went to New York City for three nights in April, and then did this four-night family trip to Maine in August. I’m crossing my fingers we can fit in one more little getaway this year, but we shall see. I do love to take Brady on vacations, because he makes everything more memorable. And I’m so glad now he’s officially been to where his dad grew up!

Thanks for reading about our first family trip to Maine. Hope you have a wonderful day!

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Questions of the day for you

Have you ever been to Maine?

What’s one place on your vacation bucket list?