Ultimate 3 Day Fall Getaway in Portland, Maine for Families

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Fall on the east coast in New England is magical, and my favorite time of year to explore Portland Maine, in the United States. This charming coastal city has lots to offer your family. Vibrant foliage, crisp sea air & lots of indoor and outdoor kid friendly activities you can explore on a 3-day adventure. 

Whether you’re strolling through historic streets of the Old Port, savoring local foodie delights (lobster rolls & famous potato donuts anyone?), or exploring scenic nature trails, & iconic lighthouses, this Fall itinerary will keep everyone happy. 

What really sells Portland Maine in Fall for us, is its blend of “big” yet small city vibe, historic charm, outdoor experiences and so many family-friendly attractions. Combine that with a bit quieter experience compared to summer, and we think it makes for the perfect mix of fun and relaxation. 

Ready to create unforgettable memories? Grab our tailored three-day plan, complete with itinerary, restaurant & accommodation recommendations, designed to help your family make the most of your vacation and the season.

QUICK OVERVIEW: FALL ITINERARY PORTLAND MAINE

Fun fact, about 40 percent of all Maine residents live in the greater Portland area. 

While many people transit through on their way to other Maine destinations like Acadia National Park & Bar Harbor, Portland, ME is worth a visit in its own right.  And we think it’s just as cool as the other Portland people rave so much about.

Here is a quick overview of the family friendly itinerary. Then I’ll get into more details below with recommendations for activities & lodging, as well as other restaurants to try.  

Day 1: Arrival & Exploring Downtown Portland

Morning:

• Breakfast at Becky’s Diner: A Portland staple, this old-school diner has hearty breakfasts perfect for fueling up.

• Explore the Old Port: Walk around the charming cobblestone streets of the Old Port District. Kids will love checking out the waterfront and the colorful shops. Or take this Discover Portland Tour by trolley ride & then a trip to Portland Head Light.

• Portland Observatory: Climb to the top of the historic observatory for panoramic views of Portland and its surrounding islands. You can also get glimpses of the vibrant fall foliage.

Afternoon:

• Early Lunch at Flatbread Company: This pizza spot is perfect for families, offering wood-fired pizzas with kid-friendly options.

• Mailboat Run Tour (12pm or 3 pm): Visit islands around scenic Casco Bay while the boat delivers actual mail

• OR Mackworth Island: Drive to nearby Mackworth Island for an easy kid-friendly hike. The island offers beautiful fall foliage views, and coastal scenery.

Evening:

• Dinner at Duckfat: Known for their fries and sandwiches, this family-friendly spot is a great way to wind down your first day. Their milkshakes are always a hit with kids!

Day 2: Fall Foliage & Outdoor Adventure

Morning:

• Breakfast at Bayside American Cafe:  Start your day with a cozy breakfast featuring family-friendly favorites like pancakes, egg benedicts, and custom omelets.

• Eastern Promenade: After breakfast, take a leisurely walk or bike ride along the Eastern Promenade. There are great views of Casco Bay and the islands, plus plenty of open space for kids to run around. 

• OR Drive to Bradbury Mountain State Park: About 30 minutes from Portland, Bradbury Mountain offers several easy hiking trails perfect for families. The summit has sweeping views of the vibrant fall foliage.

Afternoon:

• Lunch at The Honey Paw: After your morning hike, head back to Portland for a unique noodle bar experience with something for everyone, including kid-friendly options like chicken and rice. Or Sandwiches, lobster rolls or red hots (Maine hot dogs)  for the kids at Allagash Brewery.

• Children’s Museum & Theatre of Maine: Let the kids explore this interactive museum. There are hands-on exhibits and a play area for younger children, making it perfect for rainy or chilly afternoons.

Evening:

• Dinner at DeMillo’s on the Water: This floating restaurant on an old ferry is a fun experience for kids and offers great views of the harbor. The seafood and kids’ menu make it a hit for families.

Day 3: Scenic Drives & Local Farms

Morning:

• Breakfast at Tandem Coffee & Bakery: Stop by for some delicious pastries and coffee. Kids will enjoy their cinnamon buns or cookies.

• Visit a local farm & enjoy the scenic drive: Enjoy the fall foliage on your mini road trip to one of the many local farms for apple or pumpkin picking or a corn maze.

Afternoon:

• Lunch at the farm or Bahn Appetit: For local fare eat at your farm market, or try a tasty Vietnamese baguette sandwich back in Portland.

• Bug Light Park or Portland Head Light & Fort Williams Park: Head to one of these iconic lighthouses and parks for spectacular ocean views and fall colors. Or take this super popular Real Portland Tour for hidden gems & then visit 3 lighthouses. Best part, you don’t have to organize a thing!

Evening:

• Final Dinner at Great Lost Bear: End your trip with a casual, kid-friendly meal. 

This 3 day Portland Maine itinerary balances beautiful fall scenery with plenty of activities and dining options that kids and families will love. 

Here are a few more fun options if you have the time and energy:

• Take a guided Fire Truck Tour through the historic streets of Portland. 
• All in one tour Discover Portland by trolley ride & then a trip to Portland Head Light
• Enjoy a casual dinner and a bowl at Bayside Bowl
• Find a friend or babysitter to watch the kids and take a Maine Brews Cruise by bike, foot, or even by Beer Bus. 
• Rock out at a show at State Theatre
• Do some back to school shopping & visit the Boot Statue at the LL Bean flagship store in Freeport, ME (a 25 min drive).
• Try some oysters at Eventide Oyster Co.
• Check out more local breweries, to enjoy “America’s Craft Beer capital”; Belleflower Brewing, Bissell Brothers.

Read on below for all the important details of each place, recommendations for activities & lodging, as well as other restaurants to try. 

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3 DAYS IN PORTLAND, ME

A minimum of 3 days in Portland will give you a chance to experience the highlights, history and fall foliage of this city & area during the autumn months. 

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Day One – Exploring Downtown Portland 

DAY ONE – MORNING

Day one focuses on getting to know Portland, and its iconic sites, shops and historic areas. But before we get to it, there’s of course breakfast. My favourite meal of the day to eat out. 

Breakfast at Becky’s Diner

Start your day with a hearty breakfast at the local favorite, Becky’s Diner. It’s on Commercial Street near the Old Port area (about a 15 minute walk away), so handy for exploring the old part of town after your meal. 

The wild Maine blueberry pancakes are a must try, with a side of Applewood bacon and REAL maple syrup. They offer single or 3 pancakes, so easy to size up or down for the kids (or adults). The lobster roll with huge chunks of lobster meat or the haddock sandwich are always a great feed as well, if you pop in for lunch or dinner.

It can get super busy, so we recommend getting an early start if you can (they open at 5am 362.5 days a year :).

Wander Around Old Port

After breakfast, start your day walking along the cobblestone streets in Portland’s historic Old Port.  It’s lined with cool boutiques, touristy shops, coffee shops, restaurants, art galleries, bars and the wharf. Start down on Commercial Street by the water, and work your way up past Market Street.

Most stores open between 9 – 10am, although some open a bit earlier, and some a bit later. 

If you’re a fan of bookstores, I love browsing through Green Hand’s eclectic mix of used books or dog friendly Longfellow Books with local art.

For the kids, a stop into Holy Donut is always a must in our family. Gourmet potato donuts in 20 flavors, yes please! They’ll often have seasonal flavors for fall, like apple, or their triple berry holy cannoli which are fun to try. The old school cinnamon sugar donut is always my favorite though. 

There are a couple of locations, one on Commercial Street in the Old Port, and the other on Parks Avenue, down the street from a local fav park, Deering Oaks Park. 

Deering Oaks Park also hosts the Portland Farmers Market throughout the summer and into fall on Wednesday and Saturdays from 7am to 1 pm. 

🍩 There’s even A Donut Tasting Walking Tour, if you want to sample more than one shop.

LOCAL TIP: If you have a bit of time to kill before stores open, it’s well worth the visit to the Farmer’s Market & park. You’ll find mostly locally grown seasonal veggies, meat, cheese & artisan goods.

Visit the Portland Observatory

Portland Observatory is an old Maritime Signal Station built in 1807, which sits at the top of the Munjoy Hill area of Portland. Views of Portland and the surrounding ocean are amazing.

It’s a bit of a climb up to the observatory, but as it’s the last known surviving signal station of this type in the United States, it’s a great piece of history to see, as well. They’ve been open to tourists since 1939. 

The observatory offers daily tours, and is open every day at 10am – 3:30pm until mid October.

Location: 138 Congress Street.

DAY ONE – AFTERNOON

Lunch at Flatbread Company

Known for its wood-fired  pizzas made with organic ingredients, this spot is great for lunch (or dinner) with kids.

The relaxed atmosphere, open kitchen, and simple, tasty pizzas make it a favorite for families. 

While we haven’t had a chance to eat here yet, I hear great things about their Kalua Pork pizza and amazing fresh salad from a few friends who’ve tried it. You can do half and half pizzas which work well for pickier eaters if you’d like something more than just cheese.

It’s also right on the waterfront, so whether you sit inside or out, the atmosphere is fabulous.

Location: 72 Commercial Street. Open every day 11:30am to 9pm. 

LOCAL TIP: Depending on how long you hang out in the Old Port, you might want to have an early lunch at the Flatbread Company first, before the Portland Observatory.  As the restaurant is located on Commercial Street, just up the road from the Old Port area. 

Hop Aboard the Mailboat Run Tour

Just what it sounds like, the Mailboat Run tour actually delivers mail to 5 nearby islands. Making it a fun and budget friendly way to see the area. 

 If you plan on staying on the boat, it takes about 3 hours. Current departure times from Portland are 10 AM, 12 PM, and 3 PM. Double check, as times may change. 

Plan ahead & check the other boat schedules if you want to get off and explore any of the islands along the way. 

Or Hike Around Mackworth Island

If your family isn’t too keen on a boat ride, then Mackworth Island is another fun option. This island is a state park and bird sanctuary. 

There’s an easy 1.25 mile / 2 km trail that circles the whole island giving you fantastic views of the bay, fall foliage and the island wildlife itself. You can even visit an 1800’s pet cemetary and build small, hidden houses for the fairies in the community garden area.

Just a short 30 minute drive away through Falmouth, across the Presumpscot River bridge to the island. 

Location & info: Access is via Andrews Avenue off Route 1 in Falmouth. Open all year; 9:00 a.m. to sunset.  There’s a small day use fee per person.

DAY ONE – EVENING

Dinner at Duck Fat

The duck fat-fried Belgian frites (fries) and milkshakes are the reason this small spot is so popular, and for good reason. So it’s our #1 choice for dinner, or lunch, or anytime you have a snack attack.

Best fries I’ve ever had, hands down. They were so tasty, I didn’t even think to take a picture of them until they were long gone.

Can one only eat fries for dinner….I think so! But they also have salads, soups and sandwiches if you prefer. 

Location: Duckfat restaurant is at 43 Middle Street. Open 11am to 10pm every day.

The Duckfat Frites Shack (take out only) is at 43 Washington Ave. Open Sun 11am – 5pm, Mon – Thurs 11am -9pm and Sat 11am – 10pm.

Day Two – Fall Foliage & Outdoor Adventures 

Day two focuses on outdoor adventures in the morning, and some cultural activities in the afternoon.

DAY TWO – MORNING

Breakfast at Bayside American Cafe

Bayside American Cafe is a brunch institution in Portland, serving all your go-to breakfast fares, but with a Maine twist in a cute old house. 

They have a good list of egg bennies, waffles / pancakes / french toast, sandwiches, omelets, scrambles, and salad.

The Crab Cake BLTA is incredible, and the nicely seasoned and crispy home fries are the icing on the breakfast feast. 

Location: 98 Portland St. Open 7am to 2pm daily. 

Walk or Bike Along the Eastern Promenade

After breakfast, take a leisurely walk or bike ride along the Eastern Promenade. 

One of my favorite ways to see new places is to stroll their neighborhoods and trails. From this coastal pathway you can enjoy beautiful views of Casco Bay and the island, plus there’s plenty of places to stop along the way with kids. 

The Eastern Promenade Trail runs 2.1 miles / 3.4km along the waterfront. A fun place to start is from the Fort Allen side (there’s parking), and meander as far as you’d like. There’s also a beach area, and a kids playground closer to that end as well.

If you’d like to rent bikes, The Portland Encyclepedia on Commercial Street sits right on the trail, and offers kids and adult bike rentals, as well as  electric bike rentals all for reasonable prices. 

OR Hike in Bradbury Mountain State Park

About 30 minutes from Portland, Bradbury Mountain State Park offers several easy hiking trails from the west side perfect for families. Some of the trails are bike, dog and horse friendly too. 

Interesting fact, it was one of the 5 original Maine State Parks created in 1939.

The easiest trail to the summit is the Northern Loop, about 1 mile / 1.6 km.The summit has sweeping views of the vibrant fall foliage and is a pretty walk in the warmer months as well.

Info: Park hours are 9:00 AM to sunset, year-round. A small Day Use Fee per person is collected at the park entrance.

DAY TWO – AFTERNOON

Lunch at The Honey Paw

After your morning hike, head back to Portland for a unique noodle bar experience at the Honey Paw. We like to break up our meals and try something a little more adventurous.

With Asian flavors and everything from wok fried noodles, to Lobster Tom Yum soup, sticky sweet chicken wings and Mapo tofu and rice, it will add a little pizazz to your lunchtime meal. 

LOCAL TIP: If you have younger kids or pickier eaters, try Allagash Brewing Company, a snack at the Tandem Coffee House or sandwiches, barbecue dishes & appies at the Great Lost Bear. 

Explore the Children’s Museum & Theatre of Maine

After lunch, the Children’s Museum & Theatre is the perfect place to let your kids run around and explore. 

With over 3 floors of  hands-on exhibits, a play area for younger children, and different children’s plays & activities throughout the year, it makes for a perfect rainy or chilly afternoon activity. 

Location & info: Located just outside of downtown Portland at 250 Thompsons Point Rd. They’re open everyday but Tuesday 9am to 4 pm. 

LOCAL TIP: If a Children’s Museum isn’t your thing, you can try one of these:

• The Portland Museum of Art – For the artsy crowd this art museum houses over 18,000 works, focusing on old and newer influential American artists, a family sculpture park, gift shop and cafe.  It’s free for kids and youth ages 21 and under every day, and free for everyone from 4-8pm on Friday nights. 

• Tate House Museum – For history buffs, Tate House it’s the only publicly available pre-revolutionary home in the city. They offer daily tours until mid-October.

• Maine Narrow Gauge Railroad Co. & Museum – For train lovers, you can hop aboard for a scenic train ride along Casco Bay or explore the museum which features historic rail cars, exhibits and activities for children. Open daily from mid-April through late October (9:30am-4:00pm) and seasonally for events including the Polar Express.

DAY TWO – EVENING

Dinner at DeMillo’s on the Water

Demillo’s is a floating restaurant in an old ferry, making it a fun experience for families, plus the great views of the harbor help too. 

While a bit on the pricey side & touristy, the location, seafood and kids’ menu make it a hit for families. The chowder and pecan encrusted haddock are sooo good.

OTHER OPTIONS: If you’re looking for a more low-key seafood experience, there’s the flight of  lobster rolls (or a lobster roll on a stick) & kids menu from High Roller Lobster Co, or any of  the seafood chowders from Gilbert’s Chowder House (they also have grilled cheese, chicken fingers & burgers if the kids aren’t into seafood).

LOCAL TIP: The first Friday of the month from 5 – 8pm is the First Friday Art Walk. Enjoy a self guided tour through the city’s galleries, art studios & museums. There’s also  live music in Monument Square July to October. 

Day Three – Scenic Drives, Lighthouses & Local Farms 

Day three focuses on scenic fall foliage drive in the morning to a local farm with fun autumn activities such as apple picking, tractor rides, corn mazes  and tasty fall treats. 

With a visit to a lighthouse in the afternoon, because when in Maine…..

DAY THREE – MORNING

Breakfast at Tandem Coffee & Bakery 

As you will be hitting the road today, the first stop will be a quick breakfast from Tandem Coffee & Bakery. Which also happens to be in one of the cutest locations, an old gas station / laundromat turned coffee shop. 

They serve delicious baked goods (cookies, cakes, biscuits, pies etc), breakfast sandwiches and their own roasted coffee. 

Kids will enjoy their cinnamon buns for breakfast. I mean, who wouldn’t?!?

Scenic Drives & Local Farms

Is there anything better in Fall than a scenic drive with epic fall foliage? Well maybe if the kids stopped fighting….

Along the way, your family can stop at one of the many farms for apple picking, seasonal family photos, or corn mazes..  I found this epic 6 hour loop  if you want to make a day of it.

Otherwise, choose a local farm within an hour drive from Portland and enjoy the scenery along the way. Here are just a few of the many options:

• Gilsland Farm, Falmouth, (15 min drive) – Situated along the Presumpscot River estuary it’s home to the Audubon Society. There’s an environmental education center and two miles of easy trails through a salt marsh, forest,  meadow, orchard, and pond. 

• Wallingford’s Orchard, Auburn (50 min drive) – Apple picking, pumpkin patch, apple cider donuts, tractor rides, farm animals, kids play area and a corn maze. 

• Orchard Ridge Farm, Gorham (30 min drive) – Fall on the Farm Event (early Oct), apple picking, farm market, apple cider donuts, farm animals, walking trail &  kids playground

• Ricker Hill Orchards, Turner (60 min drive) – Pick your own apples and pumpkins. Apple cider donuts & baked goods, & hard cider. Activities include Disc golf,  bounce houses, a corn maze, petting zoo, tractor rides and play structures. 

DAY THREE – AFTERNOON

Lunch at the Farm or Bahn Appetit

Grab your lunch during your farm visit or head back to Portland for a meal. 

Bahn Appetit makes delicious Bahn Mi, one of the best sandwiches in the world, I think. Crusty baguette, loaded with sweet glazed meats like lemongrass beef & chicken or BBQ pork and crunchy veggies. 

They also serve up spring rolls, delicious noodle bowls, and rice plates. Definitely order the Vietnamese Iced Coffee. If you’ve never had one, it’s a strong coffee with sweetened condensed milk. Such a treat. You can thank me later. 

It’s take out only, so grab it and head back to your hotel. Or Kennedy Park is nearby to have a picnic if the weather is nice enough.  They also do delivery, so if you’re family is  tired after a long morning, head to your hotel, and order in.

Location: 171 Cumberland Ave. Open Monday to Sat. 11am – 6pm and Sun 11am to 5pm.

Visit Bug Light Park (aka Portland Breakwater Light)

Next up is a visit to Bug Light Park, a great place to see Portland’s skyline and take photos of this cute maritime light. At only 26 feet tall, it flashes every four seconds, to welcome ships into Portland’s Harbour.

There’s also a large grassy field for the kids to run around, or bring a kite and try some kite flying, a popular activity here. 

Location: Eastern end of the Greenbelt Walkway in Portland. Open daily 6am to 9pm.

OR Explore Portland Head Light & Fort Williams Park: 

If you don’t mind driving a bit more, then head to this iconic lighthouse and park.

Portland Head Lighthouse in Cape Elizabeth,  is said to to be the most photographed lighthouse in the world. Whether that’s true or not, the rocky cliffs & shoreline make for spectacular views, and photographs.

Kids can explore Fort Williams Park. There’s many things to do such as having a picnic, flying a kite, strolling the paths, walking the cliffside loop, exploring the rocky beach or Children’s Garden, or playing on the playground.

There’s even a lobster roll food truck you can grab a bite to eat at, which is open 7am – 3pm most days into early November.

Location: 1000 Shore Rd. Open year round sunrise to sunset.

LOCAL TIP: This super popular Real Portland Tour is fun as it takes you to all the hidden gems of Portland & then heads to 3 lighthouses….and you don’t have to organize a thing!

DAY THREE – EVENING

Final Dinner at Great Lost Bear

End your trip with a casual, kid-friendly meal at the Great Lost Bear. 

Spacious, with a large comfort food menu, so even the pickiest eaters can find something they’ll like. They even have a “Cub’s” menu for the kids,and a good selection of beer, if that’s your thing. 

Try their delicious buffalo or PB&J wings, burgers, or pulled pork sandwich. 

Location: 540 Forest Ave. Open 12pm to 10pm every day. 

FINAL THOUGHTS: PORTLAND MAINE IN FALL

As your ultimate 3-day fall getaway to Portland, Maine comes to a close, you’ll leave with more than just photos and souvenirs—you’ll take home treasured memories of family fun, outdoor adventures, and cozy moments.

From exploring the vibrant streets of the Old Port to enjoying nature’s stunning fall display on scenic trails, Portland offers the perfect blend of activities for everyone in the family.

Whether it’s indulging in delicious local fare, spotting lighthouses, or picking pumpkins at a local farm, each day is packed with unforgettable experiences.

Ready to plan your next visit? Maine’s charm awaits!

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