Discovering Portland, Maine: Hiking, Food, and Dog-Friendly Fun

Fort Williams Park Aug 2025

Hi! I wanted to recap my trip with my boyfriend to Portland, Maine. Maine had always piqued my interest, and I was so excited to finally visit! We went in mid-August, and the weather was perfect—chilly in the mornings and evenings but warm during the day. We decided to do Wednesday to Sunday which was the perfect amount of time. We flew out of Philly to Portland, which was just over an hour flight. The airport is super small and easy to navigate. We walked across the street to pick up our rental car, which was also a breeze!

Day 1: Arrival & Exploring Downtown

We arrived in Cape Elizabeth, where our Airbnb/VRBO was located—about a 15-minute drive from downtown Portland. Downtown has plenty of parking garages and street parking, so staying a bit outside the city worked perfectly. It was hard to find something affordable and dog-friendly downtown, so this was a great call.

After settling in, we drove into downtown Portland for lunch at Portland Lobster Co, right on the water and dog-friendly. We then walked along the coast for about 3 miles—such a beautiful introduction to the city! Exhausted, we stopped at a grocery store for snacks and returned to the Airbnb to enjoy the night with movies and takeout from a local Thai spot. I stuck with a chicken noodle soup since I was still recovering from a previous trip illness (Campylobacter), and it was fantastic!

Day 2: Beaches & Brunch

We woke up to enjoy coffee at the Airbnb, then went on a 4-mile walk starting at Kettle Cove, which connects to Crescent Beach. The trails along Crescent Beach were beautiful, perfect for a morning stroll.

• Brunch: Bayside American Café

• I spent a few hours back at Crescent Beach, soaking up the sun before it got windy and chilly in the late afternoon.

For dinner, we explored Portland for shopping, there are SO many local stores to shop in. After I finally got my Portland sweatshirt and crop top, we ended up at N To Tail, a Korean fried BBQ spot for dinner. We shared a bunch of appetizers and everything was delicious!

Day 3: Hiking & Hidden Gems

We started the day with a hike at Robinson Woods with our pup. While driving to another state park, we discovered Fort Williams Park was just 3 minutes away! It was full of trails, stunning views, and gorgeous lighthouses. There is even a section that allows dogs off leash for my dog lovers out there.

Afterward, we grabbed coffee and lunch at Scratch Baking Co—highly recommend their chicken salad sandwich, coffee, and challah bread but everything looked so good!

Later, I went back to another beach -Willard Beach (right down the road from Scratch Baking CO) for a few hours. That night, we had plans to meet a friend, but Milo, my pup got into some granola with raisins, so we ended up at urgent care. Thankfully, he was fine, and we spent the night with leftovers and takeout.

Day 4: State Parks & Lobster

We visited Two Lights State Park (small entry fee) and enjoyed walking around the water, sitting on rocks, and exploring trails. Perfect spot for a picnic with park benches and scenic views.

Later, we met our friend for coffee and then had brunch at Ocotillo—so delicious! We also discovered Hinckley Park, a dog-friendly trail near our Airbnb (dogs off-leash before 10 AM and after 3 PM). Cape Elizabeth is full of hidden gems, which made our stay even better.

• Dinner: Good Table, a charming Victorian-style restaurant. I finally had some lobster, and it was incredible!

  

  

  

  

  

  

Day 5: Departure

We headed home early the next day. Portland is such a cute town with tons to see and do, incredible food, and a great shopping scene. The city is very dog-friendly, with many restaurants offering outdoor seating. While dogs aren’t allowed on beaches during peak summer hours, there are some that allow dogs before and after hours—and outside peak season, leashed dogs are welcome most times. There is clear signage everywhere about the rules, so you will never be in doubt.

Overall: Portland was a perfect weekend getaway, with beautiful beaches, hiking trails, amazing food, and hidden gems around every corner. I can’t wait to go back!

Link to our VRBO listing