Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Hikes
United States
Connecticut
Lower Connecticut River Valley Planning Region

Portland

The best walks and hikes around Portland

4.5

(13)

195

hikers

47

hikes

Hiking around Portland, Oregon, offers access to a diverse range of natural landscapes, from expansive urban forests to dramatic river gorges and volcanic peaks. The region is characterized by dense woodlands, significant elevation changes, and numerous waterfalls. These areas provide a network of trails through state parks and natural areas, catering to various hiking preferences.

Best hiking trails around Portland

  • The most popular hiking route is Mattabesett Trail: River Road to Bear Hill Road, a 6.1 miles (9.9 km)…

Last updated: June 28, 2026

5.0

(1)

4

hikers

#1.

Mattabesett Trail: River Road to Bear Hill Road

9.87km

02:46

240m

130m

The Mattabesett Trail: River Road to Bear Hill Road offers a genuinely rugged and scenic hiking experience through Middletown, Connecticut. This moderate 6.1-mile (9.9 km) hike, with its 788 feet…

Navigate with device

Send to Phone

Save

Moderate

3

hikers

3.92km

01:03

50m

50m

The White Blaze Trail Loop in River Highlands State Park offers a delightful journey through classic Connecticut woodlands. You'll follow wide, smooth paths that gently undulate, leading you to a…

Easy
guide_signup
Let us show you the way with the komoot mobile app
With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

1

hikers

17.3km

04:50

290m

420m

The Bear Hill Loop in Middletown, Connecticut, offers a dynamic hiking experience through dense woodlands, characterized by a mix of rocky ascents and descents, open face rock sections, and occasional…

Moderate

Embark on an easy hike along the Wadsworth Mansion White Oak Lane and Dolly Lane trail, a gentle route spanning 1.0 miles (1.6 km). You will experience a modest elevation…

Easy

Embark on an easy hike along the Long Lane Multi-Use Trail, a pleasant urban path connecting downtown Middletown with the Wesleyan University campus. As you walk, you will pass by…

Easy
Sign up for free to see 43 more hikes around Portland.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Portland

MTB Trails around Portland

Road Cycling Routes around Portland

Running Trails around Portland

Cycling around Portland

Tips from the Community

Monexte
August 15, 2024, Asylum Reservoir No. 2

I'd love to visit, hike the trails, find the best viewpoints, and maybe even dig a little deeper into the background of how these reservoirs came to be. https://geometrydashmeltdown.io

0

0

River Highlands State Park features miles of trails with various overlooks of the Connecticut River. The trails on the 177-acre property are tucked against the banks of the water and in dense forest pretty much the entire time.

0

0

maniboyflex
January 26, 2024, Bear Hill

This small hill sits along the Mattabesett Trail at only 652 ft high, with a rock overcrop that offers a splendid view above the Spiderweed Preserve. This can be a nice place to watch the sunset and have a picnic.

0

0

This is an overlook area for Asylum Reservoir #2 (the most popular and largest of the 3 reservoirs). The reservoirs were originally constructed to supply water to the mental hospital nearby, which is why they are named the way they are. There are a bunch of different spots to view the lake, and the trails on the property are marked really well.

0

0

Frequently Asked Questions

What are some popular parks for hiking in and around Portland?

Portland is rich with green spaces perfect for hiking.

Forest Park is a local favorite, offering a vast urban forest experience with many trails. Washington Park is another excellent choice, known for its beautiful gardens and the Hoyt Arboretum's extensive trail network. For something unique, Mount Tabor Park offers trails on an extinct volcano with great city views. A bit further out, Silver Falls State Park is famous for its Trail of Ten Falls.

Are there any hikes with waterfalls near Portland?

Yes, the region is famous for its waterfalls, especially in the Columbia River Gorge. For a classic waterfall experience, the Wadsworth Falls via Main & Cedar Loop Trail is a great option. While many visitors flock to Multnomah Falls, other stunning options like Latourell Falls and Wahclella Falls can be found along the Historic Columbia River Highway.

Can I bring my dog on the trails?

Many trails in the Portland area are dog-friendly, but rules vary. Parks within the city like Forest Park and Powell Butte Nature Park generally allow dogs on a leash. However, some sensitive areas, such as the main loop trail at Silver Falls State Park, do not permit pets. Always check the specific regulations for the park or trail you plan to visit before you go.

What are some good family-friendly hikes?

For an easy and accessible walk with the family, the Reservoir Loop Trail — Cockaponset State Forest is a great choice. It's a short, relatively flat loop. Another excellent option is Tryon Creek State Natural Area, which has several easy trails under four miles, like the popular Triple Bridge Loop, that are perfect for children.

Are there any challenging hikes for more experienced hikers?

Yes, if you're looking for a challenge, the Mount Higby from Tynan Memorial Park hike offers significant elevation gain and rewarding views. In the Columbia River Gorge, trails like Dog Mountain and Angel's Rest are also well-known for their steep climbs and panoramic vistas.

Can I get to any trailheads using public transport?

Yes, some of Portland's best urban hiking is accessible via public transport. You can take the MAX Light Rail to Washington Park, which gives you access to miles of trails in the park itself and the Hoyt Arboretum. The 4T Trail is a unique route specifically designed to be completed using Portland's public transport system: Trail, Tram, Trolley, and Train.

What should I pack for a hike in the Portland area?

The weather in the Pacific Northwest can change quickly, so layering is key. Always bring a waterproof jacket, even if the day starts sunny. Sturdy, waterproof hiking shoes are recommended as trails can be muddy. Also, pack water, snacks, a map (or have your route downloaded on your phone), and a small first-aid kit.

When is the best time of year to hike around Portland?

You can hike year-round in Portland, but each season offers a different experience.

Summer (July-September) generally has the driest, warmest weather, making it ideal for high-elevation hikes on Mount Hood.

Spring (April-June) is perfect for wildflower viewing in the Columbia River Gorge.

Autumn (October-November) brings beautiful fall colors to urban parks like the Hoyt Arboretum.

Winter (December-March) is great for lower-elevation forest hikes, but be prepared for rain and mud. Snowshoeing is popular on Mount Hood during this time.

Are there any good circular or loop trails?

Absolutely. If you prefer to end where you started without backtracking, the Asylum Reservoir via Mattabesett Trail loop is a popular choice that circles a scenic reservoir. Many parks, like Mount Tabor and Silver Falls State Park, feature well-marked loop trails of varying lengths.

What is parking like at the trailheads?

Parking can be challenging, especially on sunny weekends at popular trailheads in the Columbia River Gorge and on Mount Hood. It's best to arrive early in the morning to secure a spot. For trails within the city, like those in Forest Park or Washington Park, consider using public transport or ride-sharing to avoid parking difficulties.

What do other hikers enjoy about the trails in Portland?

The trails around Portland are highly regarded by the komoot community, with an average score of 4.4 stars. Reviewers often praise the variety, from the lush, quiet woodlands of the state forests to the well-maintained paths along reservoirs. The accessibility of beautiful nature so close to the city is a frequently mentioned highlight.

Are there any easy hikes that still offer great views?

Yes, you don't need a strenuous climb to get a great payoff. The trails at Powell Butte Nature Park offer fantastic panoramic views of Mount Hood and the surrounding landscape with relatively little effort. Similarly, the short hikes to the viewpoints at Mount Tabor Park provide stunning vistas of the Portland city skyline, especially at sunset.

Most popular routes around Portland

Easy hikes around Portland

Most popular attractions around Portland

Places to see

Store rating

Get inspired with the komoot mobile app

With a free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Hikes in other regions.

Devil'S Hopyard State ParkMiddletownGillette Castle State ParkForster Pond State ParkChester CenterSaybrook ManorGeorge Dudley Seymour State ParkChatfield Hollow State ParkHigganumHigganum Reservoir State ParkMeshomasic State ForestCockaponset State ForestHurd State ParkLake PocotopaugDurhamStewart B. Mckinney National Wildlife RefugeMillers Pond State ParkMachimoodus State ParkRiver Highlands State ParkTrimountain State ParkEast HamptonDart Island State ParkWadsworth Falls State ParkWestbrook CenterHaddam Island State ParkMoodusConnecticut Valley Railroad State Park TrailOld Saybrook CenterDeep River CenterEssex VillageFenwickClinton

Nearby adventure guides

Things to Do in River Highlands State Park

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

© komoot GmbH

Privacy Policy