Portland hiking trails to explore

Published: May 26, 2020

From clusters of coffee shops to towering murals behind street bends, there is so much to explore in the eclectic city of Portland, Maine. 

Yet some of the city’s most beautiful spots lay intermingled throughout the town in the Portland Trail system, a giant map of over 30 green walkways and paths designed for the perfect escape from city life. While we believe you’ll love the busy center surrounding our Portland Maine Rentals properties, in this article we’d like to introduce five Portland hiking trails for when you need a change of pace.  

First, let’s cover some basics about the Portland Trail system. All thirty-one trails in Portland are maintained and sponsored by Portland Hiking Trails, which is a private 501c3 non-profit urban land trust that does not receive any tax dollars. Therefore, all of the trails maintenance comes directly from volunteers, donors, and sponsors within Portland.  

Photo courtesy of http://trails.org/our-trails/classic-trail-map/.

Before you hit the trail, here are a few basic questions new hikers to the area may have before embarking on their first adventure.  

1. Which trails have bike racks?  

According to the Portland Trails website, all paths either have a standing bike rack or a post that a cable or chain lock can attach to. A few specific trails that have dedicated bike racks include Baxter Woods, Evergreen Cemetery, Eastern Prom Trail, Western Prom, Bayside Trail, and the Back Cove Trail. 

2. Which trails are plowed for the winter?  

Since Portland Trails rely heavily on volunteer and staff support to clear different paths, the consistency of which trails are plowed can vary based on demand. Typically, the Eastern Promenade, Back Cove Trail, Deering Oaks Park, Fore River Parkway Trail, and Bayside Trail are regularly plowed in the winter. If not, it is worth mentioning that all parks welcoming snowshoeing year-round 

3. Can I reach the trails by public transportation? 

Yes! The easiest way to find which bus route is closest to your desired trail is to follow this link to the online trail map. After you locate the path you want to visit, click the “More Info” tab within the box. This will redirect you to a page listing all details of the trail including the closest METRO bus route.  

4. Which trails can I walk my dogs on?  

This is by far the most asked and simultaneously most crucial question to understand before leashing up Toto for a Sunday stroll. Given the first time violation fee is $75 for walking a dog in a restricted area, it is important to review Portland Trails infographic below 

Photo courtesy of http://trails.org/our-trails/trail-faqs-2/.

Visit this page for answers to any more questions you may have. Now let’s explore Portland Maine Rentals favorite five trails.  

1. Evergreen Cemetery 

Photo courtesy of http://trails.org/our-trails/evergreen-cemetery/.

Spanning over four miles of walking trails, Evergreen Cemetery’s 239-acre property is Maine’s second-largest cemetery. The cemetery mimics a traditional Victorian garden style, based around the theory that the pain of losing a loved one would be eased if mourning in a dreamlike garden setting. Based on the number of notable headstones, the park is included in the National Register of Historic Places. The cemeteries affiliated nonprofit group named Friends of Evergreen oversee efforts to plant flowers for deceased trust members and give insightful historical tours free to the public. 

Length: 4.1 miles 

Webpage: Click here

Dog rule: On leash at all times 

2. Back Cove Trail  

Photo courtesy of http://trails.org/our-trails/back-cove-trail/.

At just over 3.6 miles long, the Back Cove Trail is a local favorite for joggers, walkers, bikers, and strollers alike. The path features a large circle with stone dust and paved surfaces, allowing for a root free run around the cove. The trail also has ample park benches, community artwork, and breathtaking views of the city along the way to ensure a memorable experience that keeps locals coming back day after day.  

Length: 3.6 miles 

Webpage: Click here

Dog rule: On leash at all times 

3. Eastern Promenade Trail 

Photo courtesy of http://trails.org/our-trails/eastern-prom-trail/.

If you’re looking for a trail with no shortage of things to do along the way, look no further than the Eastern Promenade Trail. Built along an old railroad track, the path offers stunning views of the Maine coast. As you approach East End beach, a variety of park benches and green spaces appear–perfect for idyllic picnic lunches and frisbee games. The beach also offers a public swimming and boat launch area, proving ideal for a hot summer day or a cool autumn walk.  

Length: 2.1 miles 

Webpage: Click here  

Dog rule: On leash (exceptions apply—see chart).  

4. Fore River Sanctuary

Photo courtesy of http://trails.org/our-trails/fore-river-sanctuary/.

Featuring a lowland area, where salt and freshwater marsh meet, the Fore River Sanctuary serves as a bird watcher hotspot within the city. The 85-acre preserve is also home to Jewell Falls, Portland’s only natural waterfall. With over 5.6 miles of carefully labeled trailheads, a day spent at Fore River Sanctuary is sure to be filled with exploration and wonder over Maine’s elusive wildlife.  

Length: 5.6 miles 

Webpage: Click here

Dog rule: Varies—specific to signs placed by private owners 


5. Baxter Woods  

Photo courtesy of http://trails.org/our-trails/baxter-woods/.

The yin to Maine’s coastal yan, Baxter Woods offers stunning views of tall Maine pines throughout the thirty-acre nature preserve. Although the looped trail is a mere 0.75 miles long, it offers plentiful bird watching and picnic tables for visitors to the park. Most notably, it allows off-leash voice command of dogs, giving your pup plenty of space to roam free and enjoy the Portland woods with you.  

Length: 0.75 miles 

Webpage: Click here 

Dog rule: Voice command  

With over 70 miles of green trails to explore, there’s no shortage of reasons to explore if Portland is right for you. Visit our listings page to see beautiful apartment offerings in the area.