My Guide to Visiting Acadia and Portland, Maine in the Fall

The wedding my dear friend — and random Freshman-year roommate! — took us to beautiful Maine for the first time. I had heard wonderful things about both Portland and Acadia National Park and the state did not disappoint.

We flew into Portland and spent a night there exploring before heading to the wedding. While our stop was quick, we got to check a lot of places off our Portland list! We stayed at the Aloft right downtown, and per recommendation of the hotel bartender, we stopped by The King’s Head for lunch when we got in town. We spent some time wandering the charming streets of Portland before putting our names in for dinner at Eventide. Several people had recommended the Brown Butter Lobster Roll at Eventide, and the hype is definitely not a secret! When we showed up, there was a two hour wait for dinner, but the staff told us they would call when a table opened up. So, we decided to spend some more time exploring!

Two fun bars are right nearby: Blythe and Burrows serves up creative craft cocktails in a trendy, but cozy space. And hidden away (really, it was kind of hard to find!) is Lincoln’s — an underground, cash-only, no-frills place that’s super fun!

After those two stops, it was time for dinner! At Eventide, we ordered oysters plus those Brown Butter Lobster Rolls and GUYS…it was worth the wait.

The next morning, it was time for a quick coffee fix and then off to Auburn for the wedding festivities!

 We drove to the sweet town of Auburn for the wedding that brought us to Maine. The first several photos below are from the beautiful wedding venue, just outside town — Vista of Maine. It’s a truly magical setting for a fall wedding in New England. The changing foliage was on full display, and we got to sip cider before the ceremony.

The next morning, after the the wedding, we packed up and headed toward Acadia! We decided to take a longer route and hop on Highway 1. There are endless charming towns, and we make a couple stops along the way. One of the highlights was Five Islands Lobster Co. It was a little bit off the highway, but definitely worth the drive if you’ve got time to meander. And, we happened to stop in on the last day it was open before closing for the season. I can’t say enough about Five Islands. The lobster rolls were delicious and the whole setting overlooking the water is just spectacular. The woman working behind the counter told us her dad lobsters off the coast there, and she’s been working summers at the restaurant for years. Feels like a true Maine experience.

After lunch, we hit the road again and saw a dozen more cute towns along the way. I would’ve stopped in every one if I could!

As we got closer to Acadia National Park, I really wanted to check out the newly renovated Claremont Hotel in Southwest Harbor. New owners did a truly stunning revitalization of a historic seafront property, and it reopened in 2021. We walked the grounds, and every space is spectacularly curated. After grabbing a drink and a snack at Harry’s Bar, we headed to the town we were staying — Bar Harbor!

Bar Harbor is widely known as the most popular town for visitors planning to explore Acadia National Park. It’s one of several towns on Mount Desert Island — the home of Acadia — and when we booked this trip, I was pretty set on staying there. There are other options though, and I think we could’ve been equally as happy in some of the lesser known towns too. Bar Harbor is definitely the most lively spot on MDI. There are lots of accommodations, it’s bustling during the day and the restaurants and bars stay open into the evening. Some of the other towns we stopped through — like Southwest Harbor — certainly have restaurants and shops but they’re smaller and a bit sleepier in the evening.

We stayed at The Acadia Hotel, and it was really perfect for us. The rooms are decorated in an airy nautical theme. There’s a lovely wraparound porch, a hot tub and the hotel has outdoor gear for guest use. Breakfast is served each morning, (including made to order omelets, which Bret loved!), and it was included in our hotel cost. We also found it to be incredibly cost effective as compared to other options in Bar Harbor.

Here I want to break down the rest of the guide into suggestions for eatings, drinking and shopping….and things we loved about Acadia itself! Let’s start with activities outside the park:

Best things to do on Mount Desert Island:

  1. Side Street Cafe - This spot is known for having one of the best lobster rolls in Bar Harbor. It’s not a traditional ‘lobster pound’, like you’ll find roadside. It’s a sit down restaurant, but the lobster roll is SO GOOD. It does get busy in the evenings. We got bar seats, but you can join the online waitlist.

  2. Cottage Street Pub - We loved this small, narrow pub in Bar Harbor. The night we wandered in, the Kansas City Chiefs were playing the Buffalo Bills (we’re Chiefs fans!), and the crowd was so lively. A fun place to grab a drink!

  3. Mount Dessert Bakery - You want to talk about chocolate chip cookies? This is the place to get them on MDI. This charming bakery and coffee spot is also located in Bar Harbor, serving up all sorts of sweet treats.

  4. Mount Desert Island Ice Cream - There are about a dozen places to get ice cream in Bar Harbor, but Mount Desert Island Ice Cream has arguably the most unique flavors. They’ve also got quite a following (and a line) as a result. You can find them on the main square in town.

  5. Salt and Steel - This was one of my favorite dinners in Bar Harbor. It’s a cozy, warm space serving up seasonal flavors of Maine.

  6. Project Social Kitchen & Bar - This is a hip dinner spot in Bar Harbor. It’s in an old house, the aesthetic is lovely and the food and cocktails are divine.

  7. Dog and Pony Tavern - This is a super casual pub type spot. We stopped in for some fried food and beers after a day of hiking. They’ve got a great, secluded patio out back.

  8. Ivy Manor Inn - This is the sister property to our hotel, so we got a free drink ticket to use at Ivy Manor Inn. It’s a fun spot to grab an evening glass of wine! They’ve got a big lawn, with a fire pit and Adirondack chairs. It’s got the best kind of cozy, fall vibes.

  9. Atlantic Brewing Midtown -We grabbed beers on the Sunny, street-facing patio here. The brewery has good beers served up in a modern space with indoor and outdoor seating.

  10. Abel’s Lobster - This was another highlight on MDI. Abel’s is located on the western side of Acadia. They’ve got indoor and outdoor waterfront seating, and the lobster roll is TOP NOTCH.

Our Favorites from Acadia National Park:

  1. Beehive Trail - This is perhaps the best known of the iron-rung trails in Acadia. It’s a short climb, though you’ll go through some narrow passes. I’m a huge scaredy when it comes to heights, and I made it! The trail is a one-way loop. Once you start up, you can’t turn back. There was a park ranger warning as such at the base.

  2. Jordan Pond and South Bubble Peak - This turned out to be such a fun hike! We wanted to do the South Bubble Peak, but the closest parking was full. We parked our rental car at Jordan Pond and hiked around to the base of the South Bubble. The pond is stunning with the fall leaves reflecting on the water. And then you climb the bubble and get to see it all from above.

  3. Cadillac Mountain - If you want to drive up Cadillac Mountain between May 25 and Oct 22, you need to make a reservation. It’s easy to do, but the popular sunrise slots fill up way in advance. This one requires some advance planning!

  4. Sand Beach and Great Head Trail - The Sand Beach is a popular spot for all visitors to Acadia. It’s located down a short flight of stairs from a parking area. We met some friends and hiked the Great head Trail, through some rocky, forested areas and then popping out for another beautiful ocean view. This is a really nice hike that we had virtually to ourselves.

  5. Thunder Hole - If you’re in Acadia, you should check out Thunder Hole! It takes all of five minutes and if you catch it when the waves are really kicking up, the sound and spray of the water hitting the cavern is pretty cool.