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Trail Running Calendar near Montebello 2026-2027

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Explore the top trail runs near Montebello for 2026-2027! We've gathered 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
30
Su

The Orchard Dash 10k

Trail Run 5 km 10 km
A 5K and 10K plus multiple virtual options on a new course at Albemarle CiderWorks in North Garden, VA, with cider available after the race.
September 2026
Sep
12
Sa

Odyssey Trail Running Rampage

Trail Run 6 mi 13 mi 26 mi 50 km
Trail races at Douthat State Park featuring a roughly 13-mile loop used for a 50K, marathon, half marathon, and a six-mile race, with multiple aid stations, loop-based finisher rules, and limited field sizes.
Sep
17-20
Th - Su

Grindstone Running Festival by Utmb

Trail Run UTMB 20K/50K/100K/100M Half Marathon 50 km 100 km 167 km
A multi-distance trail event in the Shenandoah Valley with technical mountain courses and qualification opportunities for UTMB World Series Finals and Western States.
Sep
19
Sa

Nasty 9 Trail Run

Trail Run 4 mi 9 mi
Trail race at Brushy Hills near Lexington, Virginia on September 19, 2026 offering 9 mile and 4 mile courses on single track trails.
October 2026
Oct
24
Sa

Crozet Trails Crew 5k Trail Run

Trail Run 5 km 10 km
Fundraiser at Crozet Park with a 5K, 10K and 0.75 mile family run, race shirts, pancake breakfast, awards and a post race trails festival.
November 2026
Nov
7
Sa

UltraTrax Wintergreen

Trail Run 7 mi 14 mi 21 mi 28 mi
A timed, non competitive trail event at Wintergreen offering 7, 14, 21 and 28 mile loop options. Participants can add weighted vests, face a 10 hour cutoff for awards, and expect on site parking and finisher items.
Nov
7
Sa

Chessie Trail Marathon

Trail Run 5 km 10 km 13 mi 26 mi
Trail races on the Chessie Nature Trail near Lexington VA, featuring marathon, half, 10K, 5K and a relay on a smooth gravel and grass course with aid stations and medals.
Nov
7
Sa

Mountain Masochist Trail Run 50 Miler

Trail Run 50 km 50 mi 100 km
Mountain Masochist Trail Run in Montebello VA offers 100K, 50 Miler and 50K routes through Blue Ridge single track and forest roads with site specific camping available.
Nov
7
Sa

Great Eastern Endurance Run

Trail Run 10 mi 20 mi 40 mi
Trail races at Sherando Lake, VA offering 40 mile, 20 mile, and 10 mile courses on technical mountain singletrack with aid stations and enforced cutoffs.
Nov
8
Su

Harvest Hustle 10k - North Garden

Trail Run 5 km 10 km
Trail 5K and 10K races at Walnut Creek Park near Charlottesville on November 8, 2026, with virtual entry options and different medal and shirt choices.
March 2027
Mar
20
Sa

Bel Monte Endurance Races

Trail Run 25 km 50 km 50 mi
A spring mountain trail event in the Blue Ridge Mountains on March 20, 2027, offering 50 mile, 50k and 25k races on mostly single track and forest roads, with limited entries and cabins at the start finish.
April 2027
Apr
10
Sa

James River Trail Runs

Trail Run 10 mi 50 km 50 mi
Loop-format trail races at James River State Park in April offering 10 miles, 50K, and 50 miles with river sections, two aid stations, relays, and pacer options.
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