Explore Portland, CT
Portland at a Glance
Part of Middlesex County
If you’re looking for the best hiking trails in Portland this is the complete guide to all the long trails, waterfalls, and history it has to offer.
Portland has hiking 16 areas for 18 miles of trails.
My Highlights
- The natural splendor of Diana’s Pool
- The Orchard Hill overlook in Goodwin State Forest
- Watching the forest regrow at Two Sisters Preserve
Hiking
Town Parks
- Portland Reservoir Rim Trail – ★★– 2 miles – Pretty easy loop hike using old woods roads around the reservoir with lots of water features
- Riverfront Park – Unexplored
Land Trust
- Middlesex Land Trust
- Abe Tempkin Preserve –Unexplored
- Cedar Meadows Preserve –Unexplored
- Collins Preserve – ★★– 0.5 miles – Short loop with homestead ruins and water crossings
- General Hoar Preserve –Unexplored
- Oak Ledges Preserve –★★– 0.7 miles – Rugged short loop up ledges and out to a meditation shelter
- Palmer Taylor Preserve –★★– 2.3 miles – Somewhat rough trails through varied terrain and possibility for a waterfall
- Pecausett Meadows Preserves –Unexplored
- Rattlesnake Brook Preserve –Unexplored
- Sterry Preserve –Unexplored
- Middlesex Land Trust
State Parks / Forest
- Air Line Trail State Park
- Current map of extension in progress
- Medium sized lot near 82 Middle Haddam Rd, Portland, CT
- Small lot near 179 Breezy Corners Rd Portland, CT
- Connection to Palmer Taylor Preserve
- Meshomasic State Forest –★★– 3 miles – Varied old woods roads, trails, and connections in the Webb Swamp Area
- Pequsett Meadows Marsh WMA – Unexplored
- Wangunk Meadows WMA – Unexplored
- Air Line Trail State Park
Blue Blaze
- Shenipsit Trail
- South Terminus at Great Hill –★★★– 3.6 miles – A steep climb to a great overlook of the CT River then on to tiny waterfall below Bald Hill
- Shenipsit Trail
The Rest
- Helen Carlson Wildlife Sanctuary – Unexplored
Boating/Fishing
- Connecticut River – some access through Riverfront Park but no boat launches
The 140th oldest town in Connecticut. Portland, incorporated from Chatham in May 1841, and named from Portland, Dorsetshire, in England which was famed for quarries. Originally named Conway.
