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CTConnecticut rankings

Towns with the most trails in Connecticut

Ranked by miles of mapped hiking and walking trails per square mile of town. 34 towns with 2,500+ residents.

U.S. Census ACS 2020–2024 5-year

Map of Derby
Connecticut · Most trails

Where Derby lands: #7 of 34

2.3 mi / sq mi · Visit Derby →

Glastonbury 1 Glastonbury Capitol Planning Region 3.4 mi / sq mi Trail miles 174.3 mi New Haven 2 New Haven 2.7 mi / sq mi Trail miles 53.1 mi Chester 3 Chester Lower Connecticut River Valley Planning Region 2.7 mi / sq mi Trail miles 44.5 mi
#TownTrail miles per sq miTrail milesParks & preserves
1 Glastonbury GlastonburyCapitol Planning Region · 35,293 people 3.4 mi / sq mi 174.3 mi 185
2 New Haven New Haven134,349 people 2.7 mi / sq mi 53.1 mi 72
3 Chester ChesterLower Connecticut River Valley Planning Region · 3,825 people 2.7 mi / sq mi 44.5 mi 13
4 West Hartford West HartfordCapitol Planning Region · 63,620 people 2.5 mi / sq mi 56.1 mi 23
5 Map of Bloomfield BloomfieldCapitol Planning Region · 21,754 people 2.5 mi / sq mi 65.7 mi 27
6 Ansonia Ansonia19,033 people 2.4 mi / sq mi 15.1 mi 11
7 Map of Derby Derby12,487 people 2.3 mi / sq mi 12.3 mi 7
8 New Hartford New HartfordNorthwest Hills Planning Region · 6,675 people 2.1 mi / sq mi 78.9 mi 17
9 Durham DurhamLower Connecticut River Valley Planning Region · 7,208 people 2.1 mi / sq mi 49.0 mi 19
10 East Hampton East HamptonLower Connecticut River Valley Planning Region · 12,925 people 2.0 mi / sq mi 71.6 mi 18
11 Map of Middletown Middletown47,958 people 1.9 mi / sq mi 81.3 mi 31
12 Meriden Meriden60,545 people 1.9 mi / sq mi 44.2 mi 28
13 Granby GranbyCapitol Planning Region · 11,184 people 1.7 mi / sq mi 68.1 mi 34
14 Hartford Hartford121,127 people 1.5 mi / sq mi 27.5 mi 34
15 Naugatuck Naugatuck31,800 people 1.5 mi / sq mi 23.9 mi 21
16 Shelton Shelton41,889 people 1.4 mi / sq mi 45.3 mi 47
17 Ashford AshfordNortheastern Connecticut Planning Region · 4,226 people 1.4 mi / sq mi 55.4 mi 23
18 Map of Barkhamsted BarkhamstedNorthwest Hills Planning Region · 3,678 people 1.4 mi / sq mi 53.7 mi 13
19 Map of Wallingford WallingfordSouth Central Connecticut Planning Region · 44,362 people 1.4 mi / sq mi 53.9 mi 45
20 Windsor WindsorCapitol Planning Region · 29,468 people 1.3 mi / sq mi 41.3 mi 45
21 New Britain New Britain74,223 people 1.2 mi / sq mi 16.1 mi 17
22 Bridgeport Bridgeport149,153 people 1.1 mi / sq mi 20.8 mi 31
23 Danbury Danbury87,263 people 1.1 mi / sq mi 47.5 mi 25
24 Bristol Bristol61,462 people 1.1 mi / sq mi 27.8 mi 23
25 Map of West Haven West Haven55,351 people 0.9 mi / sq mi 9.9 mi 17
26 Griswold GriswoldSoutheastern Connecticut Planning Region · 11,530 people 0.9 mi / sq mi 33.6 mi 7
27 Waterbury Waterbury114,869 people 0.9 mi / sq mi 24.8 mi 30
28 New London New London27,625 people 0.9 mi / sq mi 8.9 mi 17
29 Torrington Torrington35,547 people 0.8 mi / sq mi 30.3 mi 20
30 Greenwich GreenwichWestern Connecticut Planning Region · 63,856 people 0.7 mi / sq mi 47.6 mi 98
31 Norwich Norwich39,973 people 0.6 mi / sq mi 18.3 mi 66
32 Stamford Stamford137,144 people 0.6 mi / sq mi 30.7 mi 59
33 Map of Enfield EnfieldCapitol Planning Region · 41,090 people 0.5 mi / sq mi 17.8 mi 44
34 Norwalk Norwalk92,187 people 0.4 mi / sq mi 13.7 mi 56

How this ranking works

We rank every town by miles of mapped hiking and walking trails per square mile of town. Paths, bridleways, woods roads and footways in parks count; sidewalks don't. Towns need at least a mile of trail to be ranked. Trails come from OpenStreetMap, so a well-mapped town can edge out an equally trail-rich one that's mapped less thoroughly. The town with the highest figure ranks #1.

Only towns with at least 2,500 residents are ranked; Census estimates for smaller places are too uncertain. Population and income: U.S. Census Bureau American Community Survey 5-year estimates. Trails, streets and parks: © OpenStreetMap contributors (ODbL). Conserved land: USGS PAD-US. Measured within each town's Census boundary. Town photos: Wikimedia Commons, credited on each town’s page.

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