Pet-Friendly 5-Day Itinerary in Portland, ME

Day 1: Arrival and Exploration

Portland, ME

9:00AM

Dog-Friendly Breakfast at The Green Elephant

Start your day with a healthy breakfast at The Green Elephant, where the outdoor seating welcomes your furry friend.
Located in the West End, it's a short drive from downtown, or you can walk if the weather is pleasant.
USD 25, 1 hour

10:30AM

Visit the Eastern Promenade

Stroll along the Eastern Promenade, where both you and your dog can enjoy stunning views of Casco Bay.
It's an easy 10-minute drive from The Green Elephant.
Free, 1.5 hours

12:00PM

Lunch at O'Maine Studios

Grab lunch at O'Maine Studios, which offers dog-friendly outdoor seating and locally sourced dishes.
Drive 5 minutes to the studio located downtown.
USD 30, 1 hour

1:30PM

Explore Fort Allen Park

Let your dog run freely at Fort Allen Park while you take in the history and scenic views of the water.
A quick 3-minute drive or a leisurely 15-minute walk from O'Maine Studios.
Free, 1 hour

3:00PM

Dog-Friendly Shopping on Commercial Street

Stroll down Commercial Street where pet-friendly shops like ‘Ruffwear’ welcome your dog inside as you browse for souvenirs.
It’s just a 5-minute drive from Fort Allen Park.
varies, 1.5 hours

5:00PM

Dinner at Shipyard Brewing Company

Enjoy dinner at the Shipyard Brewing Company, which features a dog-friendly patio where you can relax with a brew on a sunny evening.
A brief 5-minute drive from Commercial Street.
USD 50, 2 hours
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Day 2: Art and Nature

Portland, ME

9:00AM

Breakfast at Tandem Coffee Roasters

Start your day with locally roasted coffee and pastries on their dog-friendly patio.
Just a short drive of 10 minutes from your accommodation.
USD 20, 1 hour

10:30AM

Visit the Portland Museum of Art

Explore the Portland Museum of Art, which features beautiful sculptures and landscapes—dogs are welcome in the outdoor areas.
10-minute drive from Tandem Coffee Roasters.
USD 18, 1.5 hours

12:00PM

Lunch at Bayside Bowl

Have a fun lunch while bowling at Bayside Bowl, where you can dine on gourmet pizza with the dog by your side.
An easy 5-minute drive from the museum.
USD 35, 1.5 hours

1:30PM

Play at Deering Oaks Park

Enjoy the greenery at Deering Oaks Park where you can relax and let your dog socialize.
Only a 10-minute drive from Bayside Bowl.
Free, 1.5 hours

3:00PM

Dog-Friendly Brewery Hop

Visit local breweries like Bissell Brothers and Allagash, both of which are dog-friendly and offer unique craft beers.
Both breweries are located close to each other in a 5-minute driving radius.
USD 25, 2 hours

5:30PM

Dinner at Eventide Oyster Co.

Savor fresh seafood on the patio while your dog enjoys the fresh sea breeze. Their lobster roll is a must-try!
A short 7-minute drive from the breweries.
USD 60, 2 hours
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Day 3: Day Trip to Freeport

Freeport, ME

9:00AM

Breakfast at Wild Oats Bakery and Cafe

Fuel up with a hearty breakfast at Wild Oats Bakery, known for its welcoming dog policy and scrumptious baked goods.
Take a 30-minute drive to Freeport. Follow I-295 N to Exit 20.
USD 20, 1 hour

10:30AM

L.L. Bean Outlet Visit

Explore the L.L. Bean flagship store; dogs are welcome throughout, making it a great stop for pet-friendly shopping.
Just a short drive from the bakery to the outlet.
Free, 1 hour

12:00PM

Lunch at Freeport’s Buck’s Naked BBQ

Savor some smoky barbecue on the outside seating where dogs are welcome.
Only 5 minutes from L.L. Bean.
USD 35, 1 hour

1:30PM

Wolfe’s Neck Woods State Park

Take your dog on beautiful trails along the coast at Wolfe’s Neck Woods State Park, where nature meets adventure.
Only a 10-minute drive from Buck’s Naked BBQ.
USD 6 (parking fee), 2 hours

4:00PM

Visit Freeport Dog Park

Let your dog burn off some energy at the Freeport Dog Park right after your nature hike.
A quick 5-minute drive from the state park.
Free, 1 hour

5:30PM

Dinner at The Muddy Rudder

Finish your day with a lovely riverside dinner at The Muddy Rudder featuring a dog-friendly patio with incredible views.
A 15-minute drive back to the restaurant.
USD 50, 1.5 hours
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Day 4: Beach Day in Cape Elizabeth

Cape Elizabeth, ME

9:00AM

Breakfast at Scratch Bakery

Start your beach day with fresh pastries and coffee, all dog-friendly at Scratch Bakery.
A quick 20-minute drive from Portland to Cape Elizabeth.
USD 20, 1 hour

10:30AM

Visit Crescent Beach State Park

Spend the morning at Crescent Beach, where dogs are allowed before 9 AM and after 5 PM on-leash. Enjoy the sand and surf!
Only 10 minutes from Scratch Bakery.
USD 6 (parking fee), 2.5 hours

1:00PM

Lunch at The Good Table

Dine at The Good Table, known for its farm-fresh ingredients and dog-friendly outdoor seating.
A 5-minute drive back towards town from the beach.
USD 40, 1.5 hours

2:30PM

Explore Fort Williams Park

Visit the iconic Portland Head Light at Fort Williams Park, where dogs will love the expansive green areas to explore.
Just a 10-minute drive from the restaurant.
Free, 1.5 hours

4:30PM

Dog Walk & Play at the Beach

End the day with a leisurely walk at the beach; dogs can enjoy the sands and the cool ocean water.
A quick drive back to Crescent Beach.
Free, 1.5 hours

6:00PM

Dinner at The Lobster Shack

Enjoy fresh lobster rolls outdoors at a dog-friendly spot with ocean views.
An easy 5-minute drive to the restaurant.
USD 50, 2 hours
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Day 5: Relax and Recap

Standish, ME

9:00AM

Breakfast at the Doghouse

Indulge at the locally famous Doghouse for breakfast sandwiches that are so good that you might need to have one for your pup too!
It's a short 20-minute drive from Portland into Standish.
USD 25, 1 hour

10:30AM

Visit Sebago Lake State Park

Explore the lush trails at Sebago Lake State Park with your dog; it’s a great day for a hike or lake activities.
Just a 30-minute drive from your breakfast spot.
USD 6 (parking fee), 3 hours

1:00PM

Lunch at the Campfire Grill

Enjoy lunch at the Campfire Grill with a cozy atmosphere and a dog-friendly outdoor area.
Only 15 minutes from Sebago Lake.
USD 30, 1.5 hours

2:30PM

Relax at Standish Dog Park

Let your pup play and socialize at Standish Dog Park, a great way to wind down before heading back home.
A quick 5-minute drive from lunch.
Free, 1 hour

4:00PM

Visit a Local Winery

Wrap up your trip with a visit to a local winery like Cellar Door Winery which welcomes dogs for a relaxing afternoon.
Only 15 minutes from the dog park.
USD 20 (tasting fee), 2 hours

6:00PM

Farewell Dinner at The Village Tavern

Enjoy a heartwarming farewell dinner at The Village Tavern before concluding your trip, and their local dishes are sure to leave you satisfied.
Just 10-minute drive from the winery.
USD 45, 2 hours
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