Discover the Serenity of Olivia's Overlook
Explore the stunning vistas and serene trails of Olivia's Overlook in the heart of the Berkshires, a must-visit destination for nature lovers.
Nestled in the picturesque Yokun Ridge, Olivia's Overlook is a breathtaking hiking destination that offers stunning views of the Berkshire landscape, perfect for nature lovers and adventure seekers alike. Whether you're an experienced hiker or a casual walker, this trail is designed to provide a serene escape into nature's beauty.
A brief summary to Olivia's Overlook
- Yokun Ridge South, Hiking Trails, West Stockbridge, MA, 01266, US
- +1413-499-0596
- Visit website
Local tips
- Visit early in the morning to avoid crowds and enjoy the tranquility of the trails.
- Pack plenty of water and snacks to stay energized during your hike.
- Wear sturdy hiking shoes for better traction and comfort on the trails.
- Bring a camera or binoculars to capture the stunning views and spot local wildlife.
- Check the weather forecast before your visit, as conditions can change quickly in the mountains.
Getting There
-
Car
If you're traveling by car, start by navigating to the town of West Stockbridge, MA. From downtown West Stockbridge, head south on Main Street (Route 41). Continue for about 1.5 miles until you reach Yokun Ridge South trailhead on your right. There is a small parking area available. Please note that parking may be limited, so arriving early is recommended.
-
Public Transportation
To reach Olivia's Overlook using public transportation, take the Berkshire Regional Transit Authority (BRTA) bus that serves the area. You can board the bus in Great Barrington or Pittsfield, depending on your location. Get off at the 'West Stockbridge' stop. From there, it's a 1.5-mile walk south on Main Street (Route 41) to reach the Yokun Ridge South trailhead. Be prepared for a scenic walk along the road, and ensure you have a map or GPS for guidance.
-
Bike
For those who prefer biking, you can cycle to Olivia's Overlook from nearby towns. If you’re coming from Great Barrington, take Route 41 north. It's approximately a 6-mile ride, and you'll enjoy the beautiful scenery along the way. Once you arrive at the Yokun Ridge South trailhead, you can park your bike in the designated area.
Discover more about Olivia's Overlook
Iconic landmarks you can’t miss
Wheatleigh
3.1 km
Discover Wheatleigh, a luxurious hotel in Lenox, MA, offering elegant accommodations and a stunning backdrop of the Berkshires for an unforgettable getaway.
The Kemble Berkshires
4.5 km
Experience the historical elegance of The Kemble Berkshires in Lenox, Massachusetts, where history meets comfort in the stunning Berkshires.
Blantyre
6.7 km
Experience the elegance of Blantyre, a luxurious hotel in the Berkshires offering stunning architecture, exquisite dining, and breathtaking natural surroundings.
National Shrine of The Divine Mercy, Stockbridge, MA
7.3 km
Discover tranquility and spiritual renewal at the National Shrine of The Divine Mercy in Stockbridge, MA, a sacred place of reflection and devotion.
Schantz Galleries Contemporary Glass
8.2 km
Explore the enchanting world of contemporary glass art at Schantz Galleries in Stockbridge, where creativity and craftsmanship come to life.
Berkshire Mountain Lodge
9.0 km
Discover the perfect blend of relaxation and adventure at Berkshire Mountain Lodge, nestled in the scenic Berkshire hills of Massachusetts.
Lee Premium Outlets
10.6 km
Discover incredible savings on designer brands at Lee Premium Outlets in beautiful Lee, Massachusetts, a top shopping destination for all tourists.
Berkshire Camino LLC
11.9 km
Experience the breathtaking landscapes and rich culture of the Berkshires with guided tours by Berkshire Camino LLC, your gateway to unforgettable adventures.
Berkshires Week
12.3 km
Explore the Berkshires with expert guidance at Berkshires Week, your go-to tourist information center in Pittsfield, Massachusetts.
Basin Pond Reserve
15.8 km
Explore the stunning trails and serene beauty of Basin Pond Reserve in Becket, MA - a perfect outdoor escape for nature lovers and hikers.
By the Way Berkshires
16.8 km
Explore the Berkshires like never before with By the Way Berkshires - your ultimate guide to local events, attractions, and hidden gems.
The Berkshires
17.6 km
Explore the breathtaking Berkshires in Massachusetts, where stunning mountain views meet rich cultural heritage and endless outdoor adventures.
Beartown State Forest Headquarters
19.3 km
Explore the untouched beauty of Beartown State Forest Headquarters, a haven for nature lovers and outdoor adventurers in Massachusetts.
Titus Mansion Ruins
20.5 km
Discover the haunting beauty of the Titus Mansion Ruins in Tyringham, Massachusetts, where history and nature intertwine in a serene atmosphere.
Wahconah Falls State Park
23.8 km
Explore the enchanting Wahconah Falls State Park in Dalton, Massachusetts, where stunning waterfalls and scenic trails await outdoor enthusiasts and nature lovers.
Unmissable attractions to see
tanglewood
2.8 km
Experience the enchanting blend of music and nature at Tanglewood, a premier tourist attraction in Lenox, Massachusetts.
Frelinghuysen Morris House & Studio
3.1 km
Explore the artistic legacy of George Morris and Suzy Frelinghuysen at this charming museum in Lenox, Massachusetts, set against the backdrop of the beautiful Berkshires.
Kennedy Park
4.6 km
Explore the natural beauty of Kennedy Park in Lenox, MA - a scenic park perfect for hiking, picnicking, and enjoying the great outdoors.
Ventfort Hall Gilded Age Mansion & Museum
4.7 km
Discover the opulence of the Gilded Age at Ventfort Hall, a historic mansion and museum offering rich insights into America's luxurious past.
Mass Audubon's Pleasant Valley Wildlife Sanctuary
4.8 km
Discover the natural beauty and wildlife of Mass Audubon's Pleasant Valley Wildlife Sanctuary, a serene escape for birdwatchers and nature lovers.
The Mount, Edith Wharton's Home
5.1 km
Explore the exquisite estate of Edith Wharton at The Mount, where literature, history, and stunning landscapes converge in Lenox, Massachusetts.
Berkshire Botanical Garden
5.7 km
Discover the breathtaking beauty of Berkshire Botanical Garden, a 15-acre paradise of diverse plant collections in Stockbridge, Massachusetts.
The Playhouse
5.9 km
Discover the historic charm of The Playhouse in Lee, Massachusetts, a cultural gem nestled in the picturesque Berkshire Mountains.
Norman Rockwell Museum
7.1 km
Explore the Norman Rockwell Museum in Stockbridge, MA, home to an extensive collection of iconic American art that captures the spirit of everyday life.
Naumkeag
7.1 km
Discover the enchanting gardens and rich history of Naumkeag, a stunning estate in Stockbridge, Massachusetts, perfect for nature and art lovers alike.
Balderdash Cellars
7.1 km
Experience the beauty and flavor of Balderdash Cellars, a picturesque winery in Richmond, Massachusetts, perfect for wine lovers and foodies alike.
Chesterwood
7.5 km
Explore Chesterwood, the historic estate of sculptor Daniel Chester French, where art meets nature in a picturesque setting in Stockbridge, Massachusetts.
Berkshire Scenic Railway Museum - Lenox Station Museum
7.7 km
Explore the fascinating history of railroads at the Berkshire Scenic Railway Museum, where vintage trains and scenic rides await in Lenox, Massachusetts.
Children's Chime Tower
7.7 km
Discover the magical Children's Chime Tower in Stockbridge, MA—an enchanting landmark of music and whimsy perfect for families and tourists alike.
Mission House
7.8 km
Explore the historic Mission House in Stockbridge, MA, a captivating museum that reveals the rich cultural heritage and stories of early American missionaries.
Essential places to dine
Alta
4.5 km
Discover Alta in Lenox: A culinary haven offering creative dishes made from fresh local ingredients in an inviting atmosphere.
Gateways Inn Restaurant
4.5 km
Discover culinary delights and cozy accommodations at Gateways Inn Restaurant in historic Lenox, Massachusetts.
Brava
4.6 km
Discover Brava in Lenox: where exquisite cuisine meets exceptional wines for an unforgettable dining experience.
Bistro Zinc
4.6 km
Experience modern French cuisine at Bistro Zinc in Lenox - where culinary artistry meets warm hospitality amidst scenic surroundings.
Firefly Gastropub
4.6 km
Experience innovative American cuisine at Firefly Gastropub in Lenox, where local flavors meet vibrant ambiance for an unforgettable dining experience.
Main Street Cafe
8.1 km
Experience delightful American cuisine at Main Street Cafe in charming Stockbridge—a must-visit destination for every traveler.
Once Upon a Table
8.1 km
Discover Once Upon a Table in Stockbridge - where American cuisine meets local charm in an inviting atmosphere.
Salmon Run Fish House
8.9 km
Discover culinary delights at Salmon Run Fish House in Lee, MA – where fresh seafood meets warm hospitality amidst scenic Berkshire beauty.
Morgan House Inn & Restaurant
8.9 km
Experience delightful American cuisine in a charming setting at Morgan House Inn & Restaurant in Lee, Massachusetts.
51 Park Restaurant & Tavern
9.1 km
Experience classic American cuisine at 51 Park Restaurant & Tavern in scenic Lee, MA - where every meal tells a delicious story.
Mazzeo's Ristorante
9.2 km
Discover authentic Italian cuisine at Mazzeo's Ristorante in Pittsfield, where each dish is crafted with passion and tradition.
Roses Restaurant
9.6 km
Experience delightful American cuisine at Roses Restaurant in Lee - your go-to spot for breakfast and brunch in the Berkshires.
District Kitchen & Bar
12.8 km
Experience delightful American cuisine at District Kitchen & Bar in Pittsfield – where taste meets ambiance.
Otto's Kitchen & Comfort
12.8 km
Discover Otto's Kitchen & Comfort in Pittsfield for a delightful brunch experience featuring American classics in a cozy atmosphere.
Barrington Brewery & Restaurant
15.4 km
Discover great food and craft beer at Barrington Brewery & Restaurant in Great Barrington - a family-friendly brewpub with local flavors.
Markets, malls and hidden boutiques
La Pace Inc
4.6 km
Explore La Pace Inc in Lenox, MA for exquisite linens and unique gifts, capturing the spirit and craftsmanship of the Berkshires.
The Gifted Child
4.6 km
Explore a whimsical world of toys and creativity at The Gifted Child in Lenox, Massachusetts. A perfect stop for families and a treasure trove of unique gifts.
The Showcase Boutique
4.9 km
Discover unique treasures at The Showcase Boutique in Lenox, MA, where local craftsmanship meets charming elegance for a memorable shopping experience.
Berkshire Picker
5.7 km
Explore Berkshire Picker in West Stockbridge for unique antique furniture and decor that tells a story, perfect for collectors and casual shoppers alike.
Retro Pop Shop
7.3 km
Explore timeless treasures at Retro Pop Shop, an antique haven in Lee, MA, where nostalgia meets unique collectibles and vintage charm.
Williams & Sons Country Store
8.1 km
Explore unique gifts and local treasures at Williams & Sons Country Store in Stockbridge, MA, where charming finds await every visitor.
The Shop Around the Corner
8.1 km
Discover unique gifts and local crafts at The Shop Around the Corner, a charming gift shop in the heart of Stockbridge, Massachusetts.
Whispered The Heart ~ Local Artisan gift shop
8.1 km
Discover the charm of Stockbridge at Whispered The Heart, a unique gift shop featuring local artisans' handcrafted treasures.
Sidetracks
8.2 km
Discover the essence of Stockbridge at Sidetracks, the charming gift shop filled with unique, locally crafted treasures for every traveler.
The Jewelry Box (Hats & Jewels of the Berkshires
8.4 km
Explore The Jewelry Box in Lee, MA for unique hats, exquisite jewelry, and unforgettable bridal accessories that capture the essence of the Berkshires.
The Uptown Store
8.4 km
Explore The Uptown Store in Lee, MA – your ultimate destination for vintage records, unique antiques, and unforgettable finds.
Christopher James Antiques and Collectables
8.5 km
Explore a treasure trove of unique antiques and collectibles at Christopher James Antiques in Lee, Massachusetts, where history and charm await.
Off Of It Gallery
8.7 km
Explore Off Of It Gallery in Lee, MA for exclusive, stylish footwear that combines comfort with unique design, perfect for every fashion-forward traveler.
Karen Keenan gifts & home
8.9 km
Explore Karen Keenan Gifts & Home in Lee, MA for unique gifts and home decor that capture the essence of local craftsmanship.
Finders Keepers
8.9 km
Explore Finders Keepers, an enchanting antique store in Lee, MA, where every visit reveals unique treasures and stories from the past.
Essential bars & hidden hideouts
The Olde Heritage Tavern
4.5 km
Experience the charm of The Olde Heritage Tavern in Lenox, where delicious food meets a cozy atmosphere, perfect for unwinding after a day of exploration.
Sloane's Tavern
5.9 km
Discover the taste of Lenox at Sloane's Tavern, where local flavors and a cozy atmosphere come together for an unforgettable culinary experience.
The Lion's Den
8.1 km
Discover the charm of The Lion's Den, a lively live music bar in Stockbridge, MA, offering craft cocktails and local talent in a cozy setting.
Locker Room Sports Pub
8.5 km
Experience the ultimate sports dining adventure at Locker Room Sports Pub in Lee, MA, where delicious food and thrilling games come together.
Cafe Triskele
8.7 km
Discover the exquisite flavors of American and French cuisine at Cafe Triskele, an upscale bistro in the heart of Lee, Massachusetts.
Moe's Tavern
8.8 km
Experience the warm hospitality and vibrant atmosphere of Moe's Tavern, a must-visit bar in Lee, Massachusetts, perfect for unwinding after a day of exploration.
Bucky's Tavern
8.8 km
Discover the lively charm of Bucky's Tavern in Lee, MA – where great drinks, local flavors, and friendly faces meet.
102 Tavern Inc
9.8 km
Experience the vibrant atmosphere of 102 Tavern Inc, a favorite bar in Lee, Massachusetts, perfect for a refreshing drink and local charm.
Common or Garden Pub
11.1 km
Experience the authentic flavors of Great Barrington at Common or Garden Pub, where local charm meets hearty fare in a welcoming atmosphere.
101 Restaurant & Bar
12.6 km
Discover the best of American and seafood cuisine at 101 Restaurant & Bar in Pittsfield, MA – a perfect blend of flavor and hospitality.
Patrick's Pub
12.7 km
Patrick's Pub: A delightful Irish pub in Pittsfield, MA, offering hearty dishes, local brews, and a vibrant atmosphere for sports fans.
Thistle & Mirth
12.8 km
Experience the charm of Thistle & Mirth, a cozy pub in Pittsfield, offering delicious pizza and a vibrant local atmosphere.
Uncorked Wine & Beer Lounge
13.0 km
Experience the finest wines and craft beers at Uncorked Wine & Beer Lounge in Pittsfield, MA – a cozy retreat for every beverage enthusiast.
Sideline Saloon
13.2 km
Discover the lively ambiance and local flavors at Sideline Saloon, a top bar in Pittsfield, MA, perfect for unwinding after your adventures.
Cim's Tavern
13.2 km
Discover Cim's Tavern in Pittsfield, MA: A vibrant sports bar and pub offering great food, drinks, and a lively atmosphere for sports fans and casual diners.
