Overlook Mountain Trailhead Tours

If you're fed up with honking horns and bustling cities, lace up your boots and head out into Mother Nature. You'll be surrounded by it when you hike Overlook Mountain Trailhead.

This trekking route is located in Woodstock, a place that has plenty of things going for it! Karma Triyana Dharmachakra Monastery, Opus 40, and Bethel Woods Museum are other popular sightseeing choices not far away when you're all done at Overlook Mountain Trailhead.

Plan a trip to see Overlook Mountain Trailhead

Price found within the past 48 hours. Click for updated prices.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Save 100% on your flight
Price was $520, price is now $370 per person
$370
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (663 reviews)
Nice property. Clean. Liked firepits.

Reviewed on Oct 31, 2025

Eastwind Windham

Eastwind Windham

2 out of 5
Save 100% on your flight
Price was $590, price is now $426 per person
$426
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.2/10 Wonderful! (62 reviews)
Not sure how there were "exceptional" ratings prior to our visit. We were in main building which is on a major road and noisy but they did provide ear plugs. Some mold in corner of shower and they must have well water because it had a sulphur odor. Parking was fine. Would not return.

Reviewed on Oct 14, 2025

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Save 100% on your flight
Price was $775, price is now $568 per person
$568
per person
Jan 10 - Jan 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
8.8/10 Excellent! (74 reviews)
The property was very nice. The staff was very friendly and accommodating. Overall our stay was great. My only complaint would be the inconvenience about morning coffee. There is no coffee pot in the rooms and no coffee in the lobby. You have to walk to another building to a bakery to purchase coffee and they don’t open until 7:00. My husband is an early riser and likes his coffee

Reviewed on Oct 13, 2025

Popular places to visit

Platte clove road.. A narrow, two-lane road that climbs 1,200 vertical feet in 1.4 miles .. Have grades as high as 24% .. If you want to travel this road it will be closed in the winter .. It's to steep for trucks to plow .. There are not guard rails so it has great views .. Low gears are better to climb it .. This logging road I think has the best trails and views of the high peaks !

Platte Clove Preserve - Catskill Center

You can take time to visit Platte Clove Preserve - Catskill Center during your travels to Elka Park.

Platte Clove Preserve - Catskill Center

Karma Triyana Dharmachakra Monastery

Learn about the local history of Woodstock with a stop at Karma Triyana Dharmachakra Monastery. Discover the mountain views while you're in the area.

Karma Triyana Dharmachakra Monastery

Byrdcliffe Barn

Byrdcliffe Barn is just one of the places to see in Woodstock, so why not enjoy the other things to explore during your travels? Amble around this relaxing area's forest or experience its art scene.

Byrdcliffe Barn

Woodstock Artists Cemetery

Enjoy a stop at Woodstock Artists Cemetery, a landmark worth seeing in Woodstock. Amble around this relaxing area's forest or experience its art scene.

Woodstock Artists Cemetery

Colony

You can get tickets for a performance at Colony during your stay in Woodstock. Amble around this relaxing area's forest or experience its art scene.

Colony

Woodstock Music Shop

4/5(1 review)

You can search for that perfect souvenir at Woodstock Music Shop during your trip to Woodstock. Discover the mountain views while you're in the area.

Woodstock Music Shop

Best Lodging Options Near Overlook Mountain Trailhead

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres

Woodstock
Beautiful, Tranquil Woodstock Mountain House in the Middle of 4 Wooded Acres
Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
10 Waterfall Way, Woodstock, NY
Woodstock Way Hotel
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!

Woodstock
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch

Woodstock
Charming Cottage Rental Near Woodstock Heated Pool, Fire Pit, Screened Porch
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi

Woodstock
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!

Woodstock
Heart of Woodstock — Unique Arts-and-Crafts Home: Outdoor Room and Heated Pool!
Woodstock House on 35 private acres Mountain Views

Woodstock House on 35 private acres Mountain Views

Woodstock
Woodstock House on 35 private acres Mountain Views
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly

Woodstock
Iconic Woodstock Home - Private, Walk to Town, Family & Pet friendly
See all 1,086 properties in Overlook Mountain Trailhead
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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