Perfect Day Trip Great Barrington, MA; Hikes, Cafes, & More!
If you’re looking for a mountain town with scenic hikes and walks, the BEST bakeries and restaurants to choose from, unique local shops, and a charming downtown to stroll – look no further than Great Barrington, Massachusetts!
This post will tell you ALL the best things to do in Great Barrington. From the super popular short hike up Monument Mountain to lesser-known trails with even better views 🤫, the best pastries outside of France 💯 👀, homemade sourdough pizza with local ingredients, and homemade ice cream, too!
If you’re wondering how I know where to go in GB (as the locals affectionately call it) – I used to live here! Right off Main Street for years.
Now living next door in Connecticut, this town is still such a special place to me and is where I drive to take a ride if I want to relax, have fun, have the best food, experience arts, culture, and beauty. I always leave feeling satisfied and fulfilled. 🙂
Whether you’re a nature lover, a history buff, or a foodie, this guide will help you craft the perfect day trip to this vibrant town! So let’s get to it…
The Perfect Day in Great Barrington
1st: Cafe/Breakfast ☕️
If you love quality cafes and baked goods, you’re in luck! There are so many great cafes to choose from in Great Barrington! Here’s the list:
- ☕️ Fuel Coffee
- ☕️ Patisserie Lenox (Great Barrington location)
- ☕️ Cafe Holli
- ☕️ Rubi’s Cafe
2nd: Choose a morning hike or walk 🥾
There’s a ton of great hiking in the Berkshires and several trails with views to choose from right in Great Barrington! ake your pick from one below!
Monument Mountain: 2.5 miles, 672 ft elevation
Start your day with a refreshing hike up Monument Mountain, a popular hike located within the 555-acre Monument Mountain Reservation. Managed by The Trustees of Massachusetts, the trails up Monument are well-maintained but it will cost you! There is a kiosk in the large parking lot where you can pay ($5) with a card.
One well-known trail is the 2.5-mile Hickey and Peeskawso Loop. Labeled ‘moderate’ on AllTrails, it’s mainly a wide path with a gentle incline until you get to the top, where there are tricky scramble spots that may have you using your hands and feet to steady yourself and climb up. If you’d like to avoid these steep spots take the loop clockwise and return that way.
Flag Rock: 3.83 miles. 797 ft elevation
Here, you’ll hike the western side of the 555-acre Monument Mountain Reservation leading to views atop Flag Rock.
Choose this hike over Monument Mountain if you want a quieter hike with much less people and one without the steep or tricky sections. You’ll take the well-marked orange-blazed trail (follow signs for The Willows Trail) all the way up!
Bartholomew’s Cobble: no dogs allowed 🙁
I want to mention one more hike here because if you want a scenic walk with views that is more of a walk than a hike, I suggest heading to Bartholomew’s Cobble, another property managed by The Trustees.
This almost 400-acre nature preserve is right outside of Great Barrington in the town of Sheffield, and if you take the wide tractor path from the parking lot (see the map!), you’ll reach a stunning vista with views of the Berkshire mountains. It is a shorter and easier option than Monument Mountain or Flag Rock.
3rd: Lunch or Early Dinner
Great Barrington has amazing places to eat. From casual to upscale, there’s something for everyone, and what I always love about the restaurants here is the focus on quality and using local ingredients.
Below are the highest-rated restaurants in GB that I back up with personal experience, too! 🌟
- Prairie Whale – A farm-to-table favorite offering fresh, seasonal dishes and a cozy ambiance.
- The Well – Known for its laid-back atmosphere and delicious comfort food.
- GB Eats – A trendy spot serving creative takes on American classics.
- Xicohtencatl Mexican Restaurant – A vibrant eatery offering authentic Mexican cuisine with fresh ingredients.
- The Old Inn on the Green – A historic tavern serving elegant, candlelit meals.
- Baba Louie’s – Famous for its wood-fired sourdough pizzas.
- Number Ten – A must-visit for steak lovers looking for a refined dining experience.
🍦Must stop in Great Barrington! SoCo Creamery🍦
Located right on Railroad Street off Main Street, never leave GB, especially on a hot day, without a stop at SoCo Creamery. Try a scoop or two of handcrafted, locally made ice cream. They source all their dairy from a fourth-generation family farm in Vermont and make their own inclusions (cookie dough, brownies, caramel) from scratch!
4th: Stroll & Shop Downtown GB 🛍️
A visit to Great Barrington is not complete if you do not park your car somewhere along Main Street and WALK. 😍 Admire the architecture of many original historic buildings and of course the numerous stores…
Strolling up and down Main Street and its cute side streets, there are tons of unique clothing, home, gift, candy shops, and art galleries. Just looking at the display windows of each shop as you stroll by, it will be impossible to not pop in just for a little peak!
🚗 Parking tip: You can park right along Main Street or any of the side streets if you find a spot OR park at the Berkshire Food Coop right off Bridge Street and walk up to Main Street.
I like to start my walk from where Bridge St and Castle St intersect Main St, and then walk north! When you reach the Prairie Whale restaurant just after Rosseter St, you’ve reached the end of the main hub of shops and restaurants.
Be sure to do the loop up and around Railroad Street for fun not-to-miss shops and a darn pretty view from the top!
5th: Art, Culture, & Entertainment Options
- The Mahaiwe Performing Arts Center – A beautifully restored 1905 theater that hosts concerts, films, and live performances.
- Mason Library – A historic library with stunning interior details and a quiet place to relax.
- Norman Rockwell Museum – Significant collection of Norman Rockwell’s original work on display in his hometown of Stockbridge which is right next to Great Barrington.
- Triplex Cinema – 4-screen movie house featuring independent films and new releases. This theater is very Great Barrington – it has a cozy neighborhood feel and is not like the big movie theaters you find in busy cities.
- Berkshire Film Festival – check the schedule for dates & tickets!
- The Guthrie Center – founded by Arlo Guthrie, which serves as a cultural hub and hosts live performances, storytelling events, and community gatherings.
- The Egremont Barn – a rustic venue and historic barn with live music and great food, too!
Bonus: Great Barrington Hidden Gems & Local Favorites
🥧 Taft Farms 🍅
An easy to miss spot outside of downtown Great Barrington, Taft Farms is a great place to grab seasonal produce, prepared meals, soup and homemade baked goods. I love stopping here in the fall for their award-winning apple cider donuts and homemade pies or in summer for their berries and heirloom tomatoes.
Berkshire Mountain Bakery 🍕
Located in Housatonic, which is right next to Great Barrington, Berkshire Mountain Bakery is worth a short detour for some of the “best bread you will ever taste”. Pick up one of their famous loaves or grab a take and bake pizza 😱 to make at home!
Guidos Fresh Marketplace
I rarely ever visit Great Barrington without stopping here. And when I lived here I spent wayyyy to much money on groceries here every week. A family-owned market since 1979 Guido’s has the most amazing grocery selection – a huge cheese shop, produce, bulk section, wine, a bakery and cafe, flower shop, and gift store!
Stop here before you leave Great Barrington to pick up snacks and/or groceries for home!
Conclusion
Great Barrington is the perfect blend of adventure, culture, and culinary delights, making it an unbeatable day-trip destination in Massachusetts. Whether you’re scaling Monument Mountain, exploring downtown’s artsy side, or indulging in delicious food, this charming Berkshires town has something for everyone and keeps you coming back for more.
Plan your visit and experience the best of what Great Barrington has to offer!
