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Trail Running Calendar near Westwood 2026-2027

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Explore the top trail runs near Westwood for 2026-2027! We've gathered 30 exciting races in the area. Check out our detailed list below to find your next local race.

August 2026
Aug
15
Sa

Watermelon Wobbler 5k

Trail Run 5 km
Aug
23
Su

Old Goat Track Club XC Classic

Trail Run 5 km
September 2026
Sep
5
Sa

TARC Fall Classic

Trail Run 10 km Half Marathon ... 50 km 50 mi
Sep
13
Su

GBTC XC Invite

Trail Run 5 km
Sep
20
Su

Arc'teryx Run Boston

Trail Run 10 km
Monthly updates for Westwood

Get new running races (and updates) in your inbox every month.
Sep
27
Su

Race for the Refuge

Trail Run Backyard Ultra 10 km 30 km
Sep
27
Su

Run for Nature - Lowell

Trail Run 5 km 10 km
October 2026
Oct
3
Sa

BLS Wolfpack 5K Cross Country Run or Walk

Trail Run 5 km
Oct
4
Su

Nick's 5K Run & Fitness Walk

Trail Run 5 km
Oct
4
Su

Houghton's Pond Trail Race

Trail Run 4 mi 7 mi
Oct
11
Su

Wayland / HFC Striders XC Festival

Trail Run 3 km 5 km
Oct
11
Su

BMS Athletic Booster Club 5K

Trail Run 3 mi
Oct
17
Sa

WWII Veterans Memorial Trail Weighted Race

Trail Run Backyard Ultra
Oct
24
Sa

Womp Romp

Trail Run 10 mi 50 km
Oct
24
Sa

Pumpkin Pacer 5k

Trail Run 5 km
Oct
24-25
Sa - Su

Dead Last Ultra

Trail Run Backyard Ultra 4 mi
Oct
25
Su

The Baystate Dirty Dog Trail Run

Trail Run 5 km
Oct
25
Su

Powisset Farm Trail Run - Fall

Trail Run 2 mi 3 mi 6 mi 9 mi
Oct
25
Su

Run for the Hills - Harvard

Trail Run 5 km
Oct
25
Su

Stairs4RTroops Gillette Stadium

Urban Trail 5 km
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