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Roberto's Pizza serves authentic, flavorful pizzas made with premium ingredients and 100% real mozzarella in a fun, friendly atmosphere perfect for casual dining.
Little Cat Lodge offers a cozy alpine-inspired retreat with seasonal, locally inspired dishes and a warm, inviting atmosphere perfect for relaxing after a day on the nearby slopes. Its rustic charm blends mountain lodge comfort with mid-century Berkshires style.
Great Barrington Bagel offers authentic New York–style bagels and creative sandwiches in a cozy, welcoming atmosphere, perfect for a satisfying breakfast or casual meal. Their fresh ingredients and unique cream cheese flavors make every bite memorable.
GB Eats in Great Barrington is a cozy, family-friendly café serving creative, made-from-scratch American breakfast classics all day—think standout dishes like potato cakes Benedict and homemade jam—with a welcoming vibe and options for vegetarians, vegans, and gluten-free diners.
Hy's Fried serves crispy fried chicken and lively cocktails in a cozy setting, transforming into a dance party after dinner. This spot offers a laid-back vibe with a fun twist, making it a favorite among locals.
The Prairie Whale offers a warm, rustic retreat in Great Barrington, serving inventive American dishes crafted from local farms and featuring house-made charcuterie—all in a cozy, reclaimed-wood space centered around a striking zinc bar.
The Bistro Box is a lively roadside eatery in Great Barrington offering fresh, handmade American classics like burgers, panini, and hand-cut fries with a modern twist, all served in a casual, friendly atmosphere loved by locals and visitors alike. Open late with vegetarian and gluten-free options.
Fuel Coffee offers expertly brewed specialty coffee and delicious pastries in a cozy, art-filled space inspired by vintage gasoline imagery, perfect for relaxing with a book or catching up with friends. Its Seattle locations blend warm ambiance with quality drinks and local flavors.
Harmony Market Deli Coffee Bakery offers wholesome, organic baked goods alongside hearty deli meals and fresh coffee, featuring local breads, plant-based proteins, and crowd-favorite treats like Boston Cream cake and pumpkin chocolate chip muffins. Enjoy fresh, made-to-order meals and daily deli specials in a welcoming local spot.
Dollar General offers a convenient selection of fresh produce, dairy, and deli items alongside a wide variety of snacks, frozen meals, and pantry staples, making it easy to find affordable ingredients and quick meal solutions all in one place.
The Well Restaurant + Bar offers a cozy dining experience with handcrafted burgers and creative dishes like buffalo cauliflower and pulled pork mac & cheese. Its vibrant atmosphere is perfect for a night out in Great Barrington.
Bizen Gourmet Japanese Restaurant and Sushi Bar in Great Barrington offers fresh, flavorful Japanese cuisine with standout sushi and an inviting, authentic ambiance that blends traditional Japanese decor with a cozy, intimate setting. Their attentive service and beautifully presented dishes make every visit special.
Catamount Mountain Resort is a four-season playground where thrill-seekers can race down one of North America’s longest dual ziplines or tackle New England’s largest aerial adventure park, while families and nature lovers enjoy scenic chairlift rides and mountain views—perfect for adventurers of all ages looking for excitement and stunning scenery.
Ski Butternut offers a family-friendly skiing experience with diverse trails and scenic views, perfect for those seeking a relaxed, affordable ski getaway. It's ideal for intermediate skiers and families looking for a fun, accessible winter adventure.
Taconic State Park – Copake Falls Area offers scenic hiking, biking, and swimming amid historic ironworks and stunning waterfalls, perfect for outdoor lovers and history enthusiasts seeking a peaceful adventure in nature.
Mount Washington State Forest offers 30 miles of rugged hiking trails, wilderness camping, and scenic mountain views, perfect for outdoor enthusiasts seeking adventure and solitude in a beautiful, forested landscape. It’s ideal for hikers, campers, and nature lovers who enjoy exploring less crowded, natural terrain.
Bash Bish Falls State Park offers a stunning 60-foot waterfall surrounded by lush forests and scenic hiking trails, perfect for nature lovers and outdoor adventurers seeking a peaceful escape and breathtaking views. Ideal for hikers, photographers, and families looking to connect with nature.
Race Brook Lodge offers a unique blend of rustic charm, live music, and immersive nature experiences, perfect for travelers seeking cultural events, hiking adventures, and peaceful retreats in the scenic Berkshires. Ideal for music lovers, wellness seekers, and outdoor enthusiasts.
Alander Mountain Trail offers a challenging hike with breathtaking views of the Berkshires and surrounding states, ideal for adventurous hikers seeking panoramic vistas. This trail is perfect for those who enjoy steep ascents and scenic rewards.
Thom Reed - UFO Park offers a unique chance to explore the site of one of America’s most famous UFO encounters in a peaceful, scenic setting. It’s perfect for UFO enthusiasts, history buffs, and curious travelers seeking a thought-provoking outdoor experience.
Catamount Aerial Adventure Park offers thrilling treetop rope courses and zip lines for all skill levels, perfect for families, friends, and adventure seekers aged 7 and up who want an active, fun-filled outdoor challenge in a beautiful forest setting.
Lake Mansfield Beach and Conservation Forest Trails offer a perfect blend of sandy beach fun and peaceful, accessible woodland walks, ideal for families, nature lovers, and anyone seeking a relaxing outdoor escape in Great Barrington. The scenic trails and lake make it great for swimming, picnics, and wildlife viewing.
| Date | Price (USD, excl. fees and taxes) | Availability |
|---|---|---|
| Oct 22, 2025 | $800 | Not Available |
| Oct 23, 2025 | $800 | Not Available |
| Oct 24, 2025 | $903 | Not Available |
| Oct 25, 2025 | $943 | Not Available |
| Oct 26, 2025 | $800 | Not Available |
| Oct 27, 2025 | $800 | Not Available |
| Oct 28, 2025 | $800 | Available |
| Oct 29, 2025 | $800 | Available |
| Oct 30, 2025 | $800 | Available |
| Oct 31, 2025 | $956 | Available |
| Nov 1, 2025 | $966 | Available |
| Nov 2, 2025 | $827 | Available |
| Nov 3, 2025 | $818 | Available |
| Nov 4, 2025 | $834 | Available |
| Nov 5, 2025 | $869 | Available |
| Nov 6, 2025 | $1013 | Not Available |
| Nov 7, 2025 | $1284 | Not Available |
| Nov 8, 2025 | $1292 | Not Available |
| Nov 9, 2025 | $994 | Available |
| Nov 10, 2025 | $925 | Available |
| Nov 11, 2025 | $885 | Available |
| Nov 12, 2025 | $880 | Available |
| Nov 13, 2025 | $934 | Available |
| Nov 14, 2025 | $1196 | Not Available |
| Nov 15, 2025 | $1233 | Not Available |
| Nov 16, 2025 | $924 | Not Available |
| Nov 17, 2025 | $867 | Available |
| Nov 18, 2025 | $844 | Available |
| Nov 19, 2025 | $845 | Available |
| Nov 20, 2025 | $902 | Available |
| Nov 21, 2025 | $1022 | Available |
| Nov 22, 2025 | $1059 | Available |
| Nov 23, 2025 | $907 | Available |
| Nov 24, 2025 | $927 | Available |
| Nov 25, 2025 | $1126 | Available |
| Nov 26, 2025 | $1328 | Not Available |
| Nov 27, 2025 | $1473 | Not Available |
| Nov 28, 2025 | $1697 | Not Available |
| Nov 29, 2025 | $1532 | Available |
| Nov 30, 2025 | $1031 | Available |
| Dec 1, 2025 | $903 | Available |
| Dec 2, 2025 | $847 | Available |
| Dec 3, 2025 | $832 | Available |
| Dec 4, 2025 | $897 | Available |
| Dec 5, 2025 | $1149 | Available |
| Dec 6, 2025 | $1118 | Available |
| Dec 7, 2025 | $886 | Available |
| Dec 8, 2025 | $830 | Available |
| Dec 9, 2025 | $808 | Available |
| Dec 10, 2025 | $822 | Available |
| Dec 11, 2025 | $896 | Available |
| Dec 12, 2025 | $1046 | Available |
| Dec 13, 2025 | $1077 | Available |
| Dec 14, 2025 | $888 | Available |
| Dec 15, 2025 | $832 | Available |
| Dec 16, 2025 | $821 | Available |
| Dec 17, 2025 | $809 | Available |
| Dec 18, 2025 | $846 | Available |
| Dec 19, 2025 | $1358 | Available |
| Dec 20, 2025 | $1454 | Available |
| Dec 21, 2025 | $1454 | Available |
| Dec 22, 2025 | $1454 | Available |
| Dec 23, 2025 | $1454 | Not Available |
| Dec 24, 2025 | $1783 | Not Available |
| Dec 25, 2025 | $2029 | Not Available |
| Dec 26, 2025 | $2710 | Not Available |
| Dec 27, 2025 | $2698 | Not Available |
| Dec 28, 2025 | $2187 | Not Available |
| Dec 29, 2025 | $1881 | Not Available |
| Dec 30, 2025 | $1956 | Not Available |
| Dec 31, 2025 | $1833 | Not Available |
| Jan 1, 2026 | $1833 | Not Available |
| Jan 2, 2026 | $1833 | Available |
| Jan 3, 2026 | $1833 | Available |
| Jan 4, 2026 | $928 | Available |
| Jan 5, 2026 | $823 | Available |
| Jan 6, 2026 | $823 | Available |
| Jan 7, 2026 | $832 | Available |
| Jan 8, 2026 | $939 | Not Available |
| Jan 9, 2026 | $1226 | Not Available |
| Jan 10, 2026 | $1277 | Not Available |
| Jan 11, 2026 | $973 | Not Available |
| Jan 12, 2026 | $853 | Available |
| Jan 13, 2026 | $839 | Available |
| Jan 14, 2026 | $841 | Available |
| Jan 15, 2026 | $1011 | Available |
| Jan 16, 2026 | $2376 | Available |
| Jan 17, 2026 | $2376 | Available |
| Jan 18, 2026 | $2376 | Available |
| Jan 19, 2026 | $936 | Available |
| Jan 20, 2026 | $875 | Available |