Before heading to Acadia National Park, spend a day or two soaking up the charm of Portland, Maine. This coastal city shines in fall with cobblestone streets, cozy coffee shops, and some of the best seafood in New England. From the iconic Portland Head Lighthouse to the food stalls and breweries downtown, Portland is the perfect first stop on your Maine fall family getaway.

Next: Bar Harbor Itinerary for Families (3 Days Near Acadia)
Then: Acadia National Park in Fall: Family-Friendly Hikes & Views

Getting to Portland

Most visitors fly into Portland International Jetport (PWM), a small and easy-to-navigate airport just 10 minutes from downtown. If you’re using points and miles, Portland is often a great redemption option thanks to multiple domestic carriers flying in daily.

Once you land, pick up your rental car (I book mine through Chase Travel℠ using points earned from the Chase Sapphire Preferred®—it includes built-in rental car coverage).

Where to Stay in Portland

We stayed at the Hyatt Place Portland–Old Port, which offers free breakfast, harbor views, and a prime location for exploring the Old Port district on foot.

The best part? You can book Hyatt stays on points for $0 using transfer partners or the Hyatt award chart. If you’re new to this, check out my post:
👉 How to Book Hyatt Stays on Points for $0

Other nearby hotels to consider:

• Portland Harbor Hotel – boutique style, close to restaurants
• Canopy by Hilton Portland Waterfront – modern rooms and great views

Where to Eat in Portland, Maine

Portland’s food scene punches way above its size—it’s a dream for anyone who loves local seafood, craft coffee, and cozy bakeries.

Here are some must-try spots for a fall visit:

Breakfast & Coffee

• The Holy Donut – Famous for Maine potato donuts (try maple or pumpkin!).
• Tandem Coffee + Bakery – Perfectly flaky biscuits and strong espresso.
• The Bakeshop – Order a breakfast sandwich and a cinnamon roll before hitting the road.

Lunch & Casual Bites

• Eventide Oyster Co. – Their brown butter lobster roll is iconic.
• Highroller Lobster Co. – Creative lobster dishes with fun sauces.
• Duckfat – Belgian fries, paninis, and milkshakes.

Dinner

• Fore Street – Farm-to-table dining with wood-fired dishes (make reservations!).
• Scales – Upscale seafood right on the water.
• Flatbread Company – Great for kids and families, located on the harbor.

Treats & Drinks

• Gelato Fiasco – Fall flavors like pumpkin pie and Maine blueberry crisp.
• Shipyard Brewing Company – Seasonal Pumpkinhead Ale is a must-try in fall.

Best Things to Do in Portland, Maine in Fall

Explore the Old Port District
Wander through cobblestone streets lined with boutiques, galleries, and local shops. Don’t miss Blanche and Mimi or Folly 101 for unique Maine-made gifts.

Visit Portland Head Lighthouse
Located in Fort Williams Park in nearby Cape Elizabeth, this is one of the most photographed lighthouses in the world—especially stunning with fall foliage. There’s also a playground and picnic area for families.

Take a Sunset Cruise or Ferry Ride
Hop on a Casco Bay Ferry for a short, scenic cruise past islands and lighthouses. Fall sunsets over the harbor are breathtaking.

Walk the Eastern Promenade Trail
A 2.1-mile path along the water with panoramic harbor views—perfect for sunrise or an easy family stroll.

Explore Arts District & Museums
If it’s chilly, head downtown to the Portland Museum of Art or browse small local galleries.

The Scenic Drive from Portland to Bar Harbor

Once you’ve soaked in Portland’s charm, it’s time to begin your 3-hour drive to Bar Harbor, the gateway to Acadia National Park.

Make the most of the drive by adding these scenic stops:

• Freeport, Maine – Home of the LL Bean flagship store and cozy coffee shops.
• Wiscasset, Maine – Stop for the famous Red’s Eats lobster roll.
• Camden Hills State Park – A short detour for stunning coastal foliage views.

If you’re traveling with kids, pack snacks from Hannaford Grocery and plan a few leg-stretching stops along the way.

Using Points and Miles to Save on Your Portland Stay

I booked our Hyatt stay through Hyatt points transferred from Chase Ultimate Rewards®, and our flights were covered with Southwest points + Companion Pass, making our Portland getaway nearly free.

If you’re new to points travel, start here:
How to Book Hyatt Stays on Points for $0
Earn the Southwest Companion Pass Over and Over

Plan the Rest of Your Maine Fall Adventure

If you’re continuing your fall road trip north, the best is still to come. After a cozy stay and great eats in Portland, head to Bar Harbor, the gateway to Acadia National Par. From oceanfront walks to easy family hikes with postcard-worthy views, these next stops showcase the very best of Maine’s coast in autumn.

Next: Bar Harbor Itinerary for Families (3 Days Near Acadia)
Then: Acadia National Park in Fall: Family-Friendly Hikes & Views