Explore the Scenic Trails of Bob's Way
Discover the natural beauty of Bob's Way in Monterey, MA – a serene hiking trail with breathtaking views and diverse wildlife.
Nestled in the heart of Monterey, Massachusetts, Bob's Way offers a breathtaking hiking experience for outdoor enthusiasts. With pristine trails and stunning views, it's a must-visit for nature lovers.
A brief summary to Bob's Way
- Monterey, Massachusetts, 01245, US
- Visit website
- Monday 12 am-12 am
- Tuesday 12 am-12 am
- Wednesday 12 am-12 am
- Thursday 12 am-12 am
- Friday 12 am-12 am
- Saturday 12 am-12 am
- Sunday 12 am-12 am
Local tips
- Wear sturdy hiking boots to navigate the varied terrain comfortably.
- Visit early in the morning for cooler temperatures and fewer crowds.
- Bring plenty of water and snacks to stay hydrated and energized during your hike.
- Keep an eye out for local wildlife; you might spot deer or various bird species.
- Take your time to enjoy the views and consider bringing a camera for stunning photos.
Getting There
-
Car
If you're driving from Great Barrington, take MA-23 E for approximately 10 miles. Merge onto MA-57 E and continue for another 4 miles. Turn right onto Main St in Monterey, then follow it until you reach the entrance to Bob's Way. There is limited parking available near the trailhead.
-
Public Transportation
Take the Berkshire Regional Transit Authority (BRTA) bus that runs from Great Barrington to Monterey. You will need to check the schedule as it may not run frequently. Once you arrive in Monterey, you can either walk or take a local taxi to reach the Bob's Way trailhead, which is about a mile away from the bus stop.
-
Walking
If you are already in Monterey and wish to walk to Bob's Way, head east on Main Street from the center of town. Continue walking for about a mile until you reach the entrance of Bob's Way. Be sure to wear comfortable shoes and bring water, especially in warmer weather.
Discover more about Bob's Way
Iconic landmarks you can’t miss
Titus Mansion Ruins
3.7 km
Discover the haunting beauty of the Titus Mansion Ruins in Tyringham, Massachusetts, where history and nature intertwine in a serene atmosphere.
The Berkshires
6.5 km
Explore the breathtaking Berkshires in Massachusetts, where stunning mountain views meet rich cultural heritage and endless outdoor adventures.
Beartown State Forest Headquarters
8.1 km
Explore the untouched beauty of Beartown State Forest Headquarters, a haven for nature lovers and outdoor adventurers in Massachusetts.
Basin Pond Reserve
12.8 km
Explore the stunning trails and serene beauty of Basin Pond Reserve in Becket, MA - a perfect outdoor escape for nature lovers and hikers.
Lee Premium Outlets
13.9 km
Discover incredible savings on designer brands at Lee Premium Outlets in beautiful Lee, Massachusetts, a top shopping destination for all tourists.
Schantz Galleries Contemporary Glass
16.3 km
Explore the enchanting world of contemporary glass art at Schantz Galleries in Stockbridge, where creativity and craftsmanship come to life.
National Shrine of The Divine Mercy, Stockbridge, MA
17.0 km
Discover tranquility and spiritual renewal at the National Shrine of The Divine Mercy in Stockbridge, MA, a sacred place of reflection and devotion.
Blantyre
18.9 km
Experience the elegance of Blantyre, a luxurious hotel in the Berkshires offering stunning architecture, exquisite dining, and breathtaking natural surroundings.
Haystack Mountain Tower
19.8 km
Explore Haystack Mountain Tower, a historical landmark offering breathtaking views and rich natural beauty in Norfolk, Connecticut.
Wheatleigh
21.2 km
Discover Wheatleigh, a luxurious hotel in Lenox, MA, offering elegant accommodations and a stunning backdrop of the Berkshires for an unforgettable getaway.
Beckley Iron Furnace State Park
21.5 km
Explore the rich industrial history and scenic beauty of Beckley Iron Furnace State Park in East Canaan, Connecticut, where the past meets natural splendor.
The Kemble Berkshires
21.6 km
Experience the historical elegance of The Kemble Berkshires in Lenox, Massachusetts, where history meets comfort in the stunning Berkshires.
Carl Great Barrington Memorial
22.0 km
Discover the historical significance of Carl Great Barrington Memorial in East Canaan, Connecticut, a serene escape into the past for every traveler.
By the Way Berkshires
24.1 km
Explore the Berkshires like never before with By the Way Berkshires - your ultimate guide to local events, attractions, and hidden gems.
Berkshire Mountain Lodge
27.0 km
Discover the perfect blend of relaxation and adventure at Berkshire Mountain Lodge, nestled in the scenic Berkshire hills of Massachusetts.
Unmissable attractions to see
Ashintully Gardens
4.0 km
Explore Ashintully Gardens, a serene oasis in Tyringham, MA, where nature's beauty flourishes and tranquility awaits.
Bidwell House Museum
5.3 km
Explore the Bidwell House Museum in Monterey, MA - a historical treasure showcasing early American life amidst stunning natural beauty.
Otis Ridge
5.9 km
Experience the charm of Otis Ridge, a family-friendly ski resort in Massachusetts offering affordable skiing and stunning mountain views.
Sandisfield State Forest
6.4 km
Explore the natural beauty of Sandisfield State Forest in Massachusetts, featuring scenic trails, swimming lakes, and endless outdoor adventures.
Tyringham Cobble Park
7.7 km
Discover the breathtaking trails and serene landscapes of Tyringham Cobble Park, a must-visit destination in the Berkshires for nature enthusiasts.
Beartown State Forest
8.1 km
Experience the breathtaking beauty and outdoor adventures at Beartown State Forest, a natural gem in Massachusetts perfect for hiking, fishing, and wildlife viewing.
Questing
9.0 km
Explore the captivating ruins and serene landscapes of Questing, a nature preserve and tourist attraction in New Marlborough, Massachusetts.
Benedict Pond Loop
10.4 km
Discover the serene beauty of Benedict Pond Loop in Great Barrington, MA - a perfect hiking destination for nature lovers and families.
Tolland State Forest
10.8 km
Discover the hidden gem of Tolland State Forest in Massachusetts, a paradise for hikers and nature lovers with pristine trails and serene lakes.
Lower Carroll Mill Trailhead
11.3 km
Explore the breathtaking trails of Lower Carroll Mill Trailhead in New Marlborough, Massachusetts, a haven for hiking enthusiasts and nature lovers.
Welcome to The Birkshires Sign
12.2 km
Discover the charming Welcome to The Berkshires Sign, your gateway to a region filled with natural beauty, cultural experiences, and outdoor adventures in Massachusetts.
Butternut Ski Area and Tubing Center
12.7 km
Experience the thrill of winter sports at Butternut Ski Area, a family-friendly ski resort in the stunning Berkshire Mountains of Massachusetts.
Umpachene Falls Park
12.9 km
Discover the breathtaking Umpachene Falls Park in Southfield, MA, where tiered waterfalls meet serene trails for an unforgettable outdoor experience.
Becket Quarry
14.4 km
Explore Becket Quarry, a historic hiking paradise in Massachusetts, showcasing stunning landscapes and rich geological history.
AsiaBarong Gallery
15.2 km
Explore the captivating Asian art and antiques at AsiaBarong Gallery in Great Barrington, where cultural heritage meets artistic expression.
Essential places to dine
The Old Inn On The Green Restaurant
8.3 km
Experience exquisite American cuisine at The Old Inn On The Green Restaurant in New Marlborough, MA - where rustic charm meets culinary excellence.
Knox Trail Inn
10.8 km
Discover Knox Trail Inn: A Historic American Restaurant & Bar in East Otis Offering Cozy Ambiance and Delicious Local Cuisine.
Roses Restaurant
14.8 km
Experience delightful American cuisine at Roses Restaurant in Lee - your go-to spot for breakfast and brunch in the Berkshires.
Cafe Adam, Bar and Restaurant
15.1 km
Experience the perfect blend of French elegance and New American flavors at Cafe Adam in Great Barrington - A culinary delight awaits you.
Barrington Brewery & Restaurant
15.1 km
Discover great food and craft beer at Barrington Brewery & Restaurant in Great Barrington - a family-friendly brewpub with local flavors.
Marketplace Kitchen Table
15.1 km
Discover delightful dining at Marketplace Kitchen Table in Great Barrington - where fresh ingredients meet cozy ambiance.
Aegean Breeze Restaurant
15.2 km
Discover the essence of Greek cuisine at Aegean Breeze Restaurant in Great Barrington - where family-friendly dining meets delicious flavors.
51 Park Restaurant & Tavern
15.3 km
Experience classic American cuisine at 51 Park Restaurant & Tavern in scenic Lee, MA - where every meal tells a delicious story.
Morgan House Inn & Restaurant
15.5 km
Experience delightful American cuisine in a charming setting at Morgan House Inn & Restaurant in Lee, Massachusetts.
Salmon Run Fish House
15.6 km
Discover culinary delights at Salmon Run Fish House in Lee, MA – where fresh seafood meets warm hospitality amidst scenic Berkshire beauty.
The Dream Away Lodge
16.1 km
Experience the charm of The Dream Away Lodge: A delightful restaurant with live music nestled in the stunning Berkshires.
The Prairie Whale
16.2 km
Experience exquisite American cuisine at The Prairie Whale in Great Barrington - where fine dining meets local charm.
The Bistro Box
16.2 km
Discover gourmet hamburgers and delightful bistro fare at The Bistro Box in Great Barrington – where every bite is a taste of local excellence.
Great Barrington Bagel Company
16.2 km
Savor freshly baked bagels at Great Barrington Bagel Company – your perfect breakfast stop in charming Massachusetts.
Momma Lo's Southern Style BBQ
16.3 km
Experience authentic Southern barbecue at Momma Lo's in Great Barrington – where every bite tells a story of flavor and tradition.
Markets, malls and hidden boutiques
Eddie Bauer Outlet
13.8 km
Explore stylish outdoor clothing at Eddie Bauer Outlet in Lee, MA - perfect for adventurers and casual wearers seeking quality apparel.
Berkshire Outlet Village
13.9 km
Discover unbeatable deals at Berkshire Outlet Village, your premier shopping destination in Lee, Massachusetts, surrounded by the beauty of the Berkshires.
Bath & Body Works
13.9 km
Discover the finest beauty products at Bath & Body Works in Lee, Massachusetts, your ultimate destination for cosmetics, candles, and gifts.
Ann Taylor Factory Store
13.9 km
Explore stylish women's clothing at the Ann Taylor Factory Store in Lee, MA, where fashion meets affordability in a delightful shopping experience.
Finders Keepers
15.5 km
Explore Finders Keepers, an enchanting antique store in Lee, MA, where every visit reveals unique treasures and stories from the past.
Karen Keenan gifts & home
15.6 km
Explore Karen Keenan Gifts & Home in Lee, MA for unique gifts and home decor that capture the essence of local craftsmanship.
Off Of It Gallery
15.7 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.
Christopher James Antiques and Collectables
16.1 km
Explore a treasure trove of unique antiques and collectibles at Christopher James Antiques in Lee, Massachusetts, where history and charm await.
The Little Store
16.1 km
Unearth hidden treasures and unique finds at The Little Store, an enchanting antique shop in Great Barrington, MA.
The Uptown Store
16.1 km
Explore The Uptown Store in Lee, MA – your ultimate destination for vintage records, unique antiques, and unforgettable finds.
The Jewelry Box (Hats & Jewels of the Berkshires
16.1 km
Explore The Jewelry Box in Lee, MA for unique hats, exquisite jewelry, and unforgettable bridal accessories that capture the essence of the Berkshires.
Boho Exchange
16.2 km
Discover unique vintage finds at Boho Exchange, a charming consignment shop in Great Barrington, MA, perfect for fashion lovers and eco-conscious shoppers.
One Mercantile
16.2 km
Experience local craftsmanship at One Mercantile, a charming home goods store in Great Barrington offering unique decor and kitchenware.
Fluff Alpaca
16.3 km
Explore Fluff Alpaca, a charming gift shop in Great Barrington, showcasing unique clothing, toys, and home goods for all ages.
Happy Place Berkshires
16.3 km
Explore unique fashion and accessories at Happy Place Berkshires—where local charm meets contemporary style in Great Barrington.
Essential bars & hidden hideouts
The Old Inn On The Green
8.3 km
Experience the rustic charm and exquisite dining at The Old Inn On The Green, a historic inn and bar in New Marlborough, Massachusetts.
102 Tavern Inc
13.9 km
Experience the vibrant atmosphere of 102 Tavern Inc, a favorite bar in Lee, Massachusetts, perfect for a refreshing drink and local charm.
Bucky's Tavern
15.5 km
Discover the lively charm of Bucky's Tavern in Lee, MA – where great drinks, local flavors, and friendly faces meet.
Moe's Tavern
15.6 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.
Cafe Triskele
15.8 km
Discover the exquisite flavors of American and French cuisine at Cafe Triskele, an upscale bistro in the heart of Lee, Massachusetts.
Locker Room Sports Pub
16.0 km
Experience the ultimate sports dining adventure at Locker Room Sports Pub in Lee, MA, where delicious food and thrilling games come together.
Bogies Restaurant & Pub
16.0 km
Discover Bogies Restaurant & Pub in Great Barrington: a perfect blend of steakhouse elegance and cozy pub vibes for an unforgettable dining experience.
Mooncloud
16.4 km
Discover the charm of Mooncloud, a cozy bar in Great Barrington, where local flavors and a warm ambiance create the perfect evening retreat for tourists.
The Lion's Den
16.5 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.
Route 8 Pub
17.7 km
Experience the warmth of Route 8 Pub in Becket, MA, where delicious comfort food meets a cozy atmosphere and local brews.
Common or Garden Pub
18.4 km
Experience the authentic flavors of Great Barrington at Common or Garden Pub, where local charm meets hearty fare in a welcoming atmosphere.
Sloane's Tavern
19.9 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 Norfolk Pub
21.3 km
Experience the charm of Norfolk at The Norfolk Pub, where delicious American fare meets a cozy atmosphere in the heart of the Historic District.
Industry Kitchen & Bar
21.7 km
Experience the best of local cuisine at Industry Kitchen & Bar, a must-visit restaurant in Canaan, Connecticut, offering fresh ingredients and a vibrant atmosphere.
The Olde Heritage Tavern
22.0 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.
Nightclubs & after hour spots
Lenox Contra Dance
21.7 km
Join the vibrant community at Lenox Contra Dance for an unforgettable evening of fun, music, and traditional folk dancing in beautiful Lenox, Massachusetts.
Lenox Club
23.0 km
Discover the Lenox Club: A Premier Night Club and Wedding Venue in the Heart of Lenox, Massachusetts, Offering Unforgettable Experiences.
TheBerkshires24-7.com
29.7 km
Experience the vibrant nightlife of Pittsfield at a lively bar featuring live music, comedy, and delicious food, perfect for a fun night out.
The Zone
47.9 km
Discover The Zone, Springfield's ultimate night club offering electrifying music, delicious drinks, and an unforgettable nightlife experience.
Upstate
48.0 km
Discover Upstate, Hudson's premier night club, where electrifying music meets vibrant nightlife in an unforgettable setting.
Dewey's Jazz Lounge
48.1 km
Discover Dewey's Jazz Lounge in Springfield, where live music meets exquisite dining in a vibrant atmosphere.
The X-Room
48.3 km
Discover the vibrant nightlife of Springfield at The X-Room, where unforgettable experiences and electrifying music come together in perfect harmony.
Bar Rated Trivia
48.9 km
Join the fun at Bar Rated Trivia in Avon, CT, where knowledge meets excitement in a lively, friendly atmosphere perfect for trivia lovers.
Wunderbar Bistro
51.3 km
Discover the delightful flavors of American cuisine at Wunderbar Bistro, Hudson's top spot for burgers, wings, and more in a cozy atmosphere.
The Hereafter
51.3 km
Experience the charm of Hudson at The Hereafter, a cocktail bar known for its creative drinks and inviting ambiance.
Park Theater
51.3 km
Experience the vibrant world of live music and performing arts at Hudson's Park Theater, where every show is a unique adventure.
Governor's Tavern
51.4 km
Experience the vibrant flavors of Hudson, NY at Governor's Tavern—your go-to spot for delicious grilled dishes, craft beers, and a lively atmosphere.
Padrona
51.9 km
Experience the best of Hudson, NY at Padrona, where exquisite cocktails and delicious dishes come together in a stylish setting.
BackBar
52.0 km
Explore the vibrant culinary scene at BackBar in Hudson, NY, featuring locally sourced dishes and a lively atmosphere perfect for any occasion.
The Maker Lounge
52.1 km
Experience the cozy atmosphere of The Maker Lounge in Hudson, where craft cocktails and creative vibes await tourists seeking relaxation.
