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.
The Hidden Inn
AutoCamp Catskills
Kaatskill Mountain Club at Hunter Mountain

Popular places to visit


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
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
Contemporary, Secluded Cabin in the Heart of  Woodstock W/Fireplace

Contemporary, Secluded Cabin in the Heart of Woodstock W/Fireplace

Woodstock
Contemporary, Secluded Cabin in the Heart of Woodstock W/Fireplace
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
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.

Things to do near Overlook Mountain Trailhead

At Overlook Mountain Trailhead in Woodstock, New York, visitors can enjoy a variety of activities including hiking the scenic Overlook Mountain, birdwatching, and attending live music events. The area is perfect for an overnight trip, allowing you to explore both the natural beauty and the unique charm of Woodstock. Don't miss the opportunity for an uphill trek that offers stunning views and a memorable outdoor experience.

Shopping

For a unique shopping experience near Overlook Mountain Trailhead, visit Woodstock Music Shop, just 2 miles away. If you're up for a drive, Hudson Valley Mall, located 10 miles away, offers a variety of stores in a vibrant setting. Vinnie's Farm Market is also nearby at 8 miles.

Recreation

Experience the serene outdoors at Woodstock Golf Club, just 2 miles from Overlook Mountain Trailhead, perfect for a round of golf. For relaxation, Saugerties Village Beach, 9 miles away, offers a tranquil setting. Indulge in rejuvenating treatments at Copperhood Retreat & Spa, located 12 miles from the trailhead.

Adventure

Experience thrilling skiing at Hunter Mountain, located 10 miles from Overlook Mountain Trailhead, perfect for winter sports enthusiasts. For a scenic hike, explore the Ashokan Rail Trail, 6 miles away, offering stunning views and outdoor adventure. North-South Lake Campground, also 10 miles away, is ideal for family fun and exploration.

Nightlife

Enjoy a night at the Ulster Performing Arts Center, just 12 miles away, for a cultural experience with family-friendly shows. For a fun evening, head to Ellenville Lanes, 27 miles away, or catch a classic film at the Overlook Drive-In Theater, 29 miles away, perfect for a romantic night out.

Find the best attractions near Overlook Mountain Trailhead

At Overlook Mountain Trailhead in Woodstock, New York, visitors can enjoy a blend of outdoor adventures and cultural experiences. Key attractions include the scenic overlook, the historic Overlook Mountain House, stunning waterfalls, and the Overlook Fire Tower, which offers breathtaking views. This area caters to families and nature enthusiasts alike, making it a perfect spot for exploring the beauty of the Catskills.

  • Kaaterskill Falls: Located 9 miles from Overlook Mountain Trailhead, Kaaterskill Falls is a breathtaking natural wonder perfect for outdoor enthusiasts. With its romantic setting and adventurous trails, you can hike to stunning viewpoints or relax by the cascading water, immersing yourself in the beauty of nature.
  • Karma Triyana Dharmachakra Monastery: Situated right at the trailhead, this serene monastery offers a glimpse into Buddhist culture. Visitors can explore the peaceful grounds, attend meditation sessions, and appreciate the intricate architecture, providing a unique spiritual experience.
  • Bethel Woods Museum: Just 4 miles away, this museum celebrates the cultural legacy of the Woodstock festival. Engaging exhibits and artifacts showcase the music and social movements of the 1960s, making it a fascinating stop for history and music lovers alike.

Best time to go to Overlook Mountain Trailhead

Visitor numbers around Overlook Mountain Trailhead is generally unchanged in popularity throughout the year. The best time to visit Overlook Mountain Trailhead can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Overlook Mountain Trailhead falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Overlook Mountain Trailhead falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.0°F (-3.9°C)Light RainMostly SunnySlightly LowSlightly Low
February26.6°F (-3.0°C)Light RainMostly CloudyAverageAverage
March34.5°F (1.4°C)Light RainMostly SunnySlightly LowSlightly Low
April46.2°F (7.9°C)Light RainMostly SunnySlightly LowSlightly Low
May57.7°F (14.3°C)Light RainMostly SunnyAverageAverage
June65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighSlightly High
September62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnySlightly HighSlightly High
November39.0°F (3.9°C)Light RainMostly SunnyAverageAverage
December31.1°F (-0.5°C)Light RainMostly CloudyAverageAverage

Booking tips and Expedia advantages for Overlook Mountain Trailhead

Save money on your trip to Overlook Mountain Trailhead by visiting during the off-peak months of January and March to April, when prices are lower. Tuesdays are the cheapest days to stay, while Saturdays tend to be the priciest. Take advantage of public transport and explore the area on foot, as entry to the trailhead is free. Utilize Expedia to find eco-certified hotels and consider package deals that combine flights and accommodations for additional savings. Joining Expedia's One Key membership can also unlock exclusive discounts and rewards for future stays.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Overlook Mountain Trailhead are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Overlook Mountain Trailhead is Tuesday. The most expensive day to stay around Overlook Mountain Trailhead is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your options based on your budget, preferred location, and the type of hotel you desire. For instance, selecting the "Eco-certified" option will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay at the Overlook Mountain Trailhead with your flights and activities through an Expedia package deal.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

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Explore a world of travel with Expedia