Distance is one measure of a hike. Elevation gain is the one that decides how your legs feel the next morning. We pulled every trail in Delaware with a measurable elevation-gain tag — out of the 843 entries OutsideAtlas tracks here — and ranked them by total vertical. The result is a roster of climbs that punch above their mileage.
Delaware is the second-smallest state — flat, low-elevation, and dominated by coastal plain. Hiking here means refuge boardwalks, beach trails, and gentle hardwood loops. The state's high point at Ebright Azimuth is 448 feet — long, flat walks dominate the trail mix. Ticks and chiggers are abundant in coastal scrub; deer ticks carry Lyme.
Our rankings here are data-driven — pulled from the 843 mapped entries OutsideAtlas tracks in Delaware — but the data has limits worth being honest about. Elevation-gain figures depend on the surveyor and the digital-elevation model used. Some trails are missing this tag entirely and are excluded from the list. Treat numbers as approximate but directionally reliable.
The Ranking
Ranked from #1 to #2. Click through any entry for the full trail page — map, elevation profile, weather forecast, and direct OpenStreetMap source link.
#1. Lost Trail / Long Trail
Lost Trail / Long Trail ranks #1 for vertical gain, sitting near Rosenhayn in Salem County. Expect ground surface on a genuinely demanding grade. Local trail-association reports tend to agree this is one of the better-maintained options in the area, which matters more on a hike of this length than on a quick walk. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Lost Trail / Long Trail trail page →Map, elevation profile, current weather, and OSM source.#2. Long Trail
Long Trail ranks #2 for vertical gain, sitting near Rosenhayn in Salem County. Expect ground surface on a genuinely demanding grade. The route is well documented in OpenStreetMap, which is what put it on our radar — community-mapped routes tend to be the ones that get hiked enough to stay open. The natural-surface tread can get slick after rain and muddy in spring — pick a dry weather window if you have the flexibility. Climbing fitness — not raw mileage — is the gating factor. Trekking poles and an early start pay off. See full trail details, map, and current weather on OutsideAtlas for the most current information.
Open the Long Trail trail page →Map, elevation profile, current weather, and OSM source.Planning your Delaware trip
A few pieces of context are worth keeping in mind specifically for Delaware. Spring and fall are ideal; summer brings humidity and biting flies in the marshes; winter is mild but bare. Ticks and chiggers are abundant in coastal scrub; deer ticks carry Lyme.
Always cross-reference the official land-manager page before driving out — closures, fire restrictions, and seasonal road access can change quickly. Our trail pages link directly back to the OpenStreetMap source so you can see the tags we're working from.
If you're new to hiking generally, our beginner's guide covers footwear, layering, and the day-pack basics. For safety planning on bigger objectives, the ten essentials guide is worth twenty minutes of reading.
More Delaware hiking guides
If you found this useful, the rest of our Delaware coverage continues below.
- Top 10 longest trails in Delaware — Multi-day routes and through-hikes ranked by distance.
- Best beginner hikes in Delaware — Easy, well-marked trails for first-time hikers.
- Most challenging hikes in Delaware — Expert-rated routes for experienced hikers only.
- Best national parks in Delaware — Federal parks and recreation areas ranked.
- Best waterfall hikes in Delaware — Trails leading to named falls, ranked by accessibility.
- Best dog-friendly hikes in Delaware — Where leashed dogs are explicitly welcome.
- Best family hikes in Delaware — Short, easy trails sized for kids and grandparents.
Rankings like this are starting points, not verdicts. Trail conditions change, new routes get tagged, and what was the toughest trail in Delaware last year might not be next year. We refresh these articles when the underlying data shifts meaningfully.
Got a correction, a route we missed, or a question? Drop us a note via the contact page. We read every email and we'd rather hear it from you than miss it.
