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    Trail Break

    4.0 (255 reviews)
    Closed 11:30 am - 8:30 pm

    Trail Break Photos

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    TRAIL BREAK ATMOSPHERE

    What's the vibe?
    Hipster
    Casual
    Trendy
    Moderate noise

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    Recommended Reviews - Trail Break

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    Margaritas were very good. They didn't skip on the rims!!
    JoAnne K.

    We stopped while visiting Woodstock. It was a Friday evening and we didn't have reservations. There were no tables inside so we were seated outside on the deck. I am Celiac, so I was questioning different items on the menu to see if they were gluten-free. The majority of the waitstaff didn't know much about whether items were gluten-free or not. They did go back to the cooks and find out. We had the chips & guacamole, and street corn cob as an appetizer. The chips for the chips and guac were mostly broken, which was disappointing, but the guacamole was very good. The tortilla chips are not gluten-free. They are made of corn, but are cooked in the same fryer as the churros which means they are cross contaminated. The street corn on the cob was excellent and we found out, gluten-free. Two of the members of our group had burritos. They were very big and well wrapped. They both enjoyed them. The rest of us had tacos. We had Carne Asada. (Excellent!), tuna (also very good) and pork (excellent!). If you don't like spice, the pork is the way to go. I ordered the chickpea and sweet potato side with my tacos. It was so spicy it was un edible. Even those in our group who like a lot of spice said it was too much and I couldn't eat it. Overall, it was a great meal. We really enjoyed ourselves. The deck was nice and I did not get sick from cross contamination. Overall, Trail Break was a winner.

    Smokey spicy sweet appetizer (guacamole, street corn salad, pineapple salsa), duck wings (SO GOOD) and maple guava lemonade.
    Hannah S.

    One of our favorite spots in the Upper Valley! They've expanded their non alcoholic beverage list and it's PHENOMENAL. Get the coconut mango limeade or the maple guava lemonade -- SO GOOD. I dream about the pineapple salsa and street corn almost every night and the shrimp and/or raw tuna tacos are to die for. Also the duck wings... oh my god. And whatever you do, do NOT leave without an order of churros. Fun, casual vibes both inside and out. Sabrina, Cindy, Alejo, and Topher are always such a joy, fantastic service!!

    Jamaican jerk flavored popcorn
    Lili S.

    The servers wear cute hats so they're easy to spot when you need assistance. You receive a complimentary bowl of Jamaican Jerk flavored popcorn for an appetizer. The tortillas used for the burritos were extremely dry. However, they made up for this by serving the best horchata in Vermont. I wasn't too excited about the QR code receipt payment style, but it's a safe assumption they'd allow for cash payments and scan cards at the front register upon request. There is ski-themed seating outside, like a ski lift in front of a large table. It's a fun restaurant for chill eats.

    Tacos and pineapple pickled salsa
    Bob H.

    Wow great spot! Sat outside and it had a cool deck with a lot of nice sunshine. Ok the food.. we had several different tacos and all were great. The pork and chicken were reeaaaally good. Also they had tons of specialty sodas and I need to go back for some brews but we had a long drive home. Great and friendly service. Will go back!

    Tess C.

    I think we came at an off night for Trail Break given the overwhelmingly positive reviews. When we arrived we were able to snag seats at the bar and our waitress came over after about 5 minutes. We ordered immediately (which was a struggle given their NIGHTMARE to read and navigate website menu) and waited about 45 minutes for our food, which was tacos and quesadillas (aka some of the quickest food to make). The blackened fish was tasty, as was the chips with salsa and guac trio, but everything else was just off. First off they were out of nearly every side they had at 7 pm on a Saturday night, and were out of two of their ~7 taco options. I ended up getting the chickpea mash side which was so sickeningly sweet it was like coated in maple syrup. I didn't like it at all. The other taco I got was the black bean, onion, cotija cheese and tater tot one. I don't know what I was thinking with that but I do not recommend. Super strange flavor combination. Would love to come back and try it again when they're having a better night. Giving it 3 stars because our waitress was super sweet and generous with extra chips, and the inside is super cute and welcoming and we were able to snag seats right away without a reservation.

    Nachos
    Shannon R.

    If there's anything more glorious than a literal pizza box full of chorizo nachos from Trailbreak, I have yet to experience it. And don't get me started on their tacos!!! They are so incredibly packed with meat, unlike anything you've seen before. It's gotten to the point where my husband and I will choose our accommodations when we travel to VT based on their proximity to Trailbreak. Delicious food served by friendly, flannel-clad Vermonters, all at an incredible value? Sign me up! Yes, you should go here, and yes, you should bring an appetite. Dare I say, one of the best destinations in VT!

    Kim D.

    Their new location next to the Quechee Gorge is great. Sweet vibe w lots of seating Tacos were delicious and the staff is fantastic! We were seated quickly and food came out fast too. Highly recommend

    Pulled chicken taco, mahi taco, pulled pork taco
    Daniella S.

    Found this spot open on a Monday evening and so glad we did! There was 10 adults and 3 kids, we were seated at a long table with 1 seat that was a ski chair, so cool. The vibes were so nice and warming. Great service. We started with some large pitcher margaritas. An original, a spicy watermelon, and a guava. The spicy watermelon was my favorite, so good and the perfect Spicy ness to it. The original was a tad too sweet *. The guava was good. We also got the duck wings, SO GOOD, Perfect sauce and crunch. We got the nachos. HUGE serving size, they were seriously exceptional. I am not a nacho fan, and these were unreal and I'd get them again. 2 types of meat on them. We then all got different tacos and plantains. The shrimp taco was good, shrimp were tiny. The chicken and pork was GREAT. The mahi was very good and fresh. For dessert we got the churros, so warm and fresh. But the tres leches we got was WOW. Super great. Loved this spot and would come back for sure!

    Andres A.

    We stopped in for dinner and were seated immediately. The restaurant is very spacious and bright. For starters we had chips with some spicy sauce, guacamole and a pineapple sauce. There was a healthy portion of chips and interestingly enough everyone at the table had a different take on which sauce was best, personally I liked the spicy one. For our entrees we had the chicken quesadillas, steak quesadillas, and a couple of serving of tacos. The chicken quesadillas were ok, the carne Asada quesadillas were a bit dry. My girlfriend enjoyed the Mahi Mahi taco but not so much the carne Asada one. The one thing they enjoyed was the sweet plantains. Overall, I think the place was ok but I don't think it would be a place I would return to.

    Le T.

    What an amazing place!! Let's taco about it! Tacos - phenomenal Street corns - off the charts Atmosphere - dope/ trendy Service - on point Price- get out! 2 tacos and a side for $13.50, definitely a steal! Come try it out!

    Nachos-demolished
    Gabriela D.

    Get the sheet pan of nachos. So good the cream and spinciness is *chefs kiss* Genevieve was our server at the bar she was cool and efficient. Perfect little ski/surf bar vibes. It's cute foods good.

    Anton E.

    I used to love this restaurant, as the food is good, but I simply cannot support them due to the actions of the owner. I had long heard rumors that the owner was a real jerk, but these rumors were confirmed via his comments on the restuarants' page. Their comments show an insensitivity to the plight of working class and service industry people as well as a disregard for their own image as a restaurant. Insulting potential customers on social media? Doesn't get more classless than that. I wouldn't give this restuarant a penny of my money. I honestly hope they try to "clap back" at me here, because I know that's how the owner finds fulfillment in life.

    Kathy M.

    Quite literally some of the best food I've ever had. I dream about the west coast burrito I had. The service was incredible and the place itself is so cute. I've already returned a few times and will continue to!!!

    a view of a bar with beer taps

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    Ask the Community - Trail Break

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    I'm so sad to have to write a negative review of Simon Pearce (although there are plenty of them…read moreout there). It was our first time there, celebrating our son's 21st birthday. Not sure what happened between the kitchen and our server, but 2 of 3 main courses came out cool. One was my crab-stuffed sole and the other was our son's $85 filet mignon. We had to let the server know. She brought over the manager who said they would "reheat" our dishes. I questioned him, um, "reheat" not remake? He said he could redo them but the steak will take 25 minutes (son's father had already dug into his duck by this point). Manager said if we try reheating it and it's not to our liking he'd take the steak (no mention of the sole) off the bill. We said fine, let's try reheating so as to resume eating asap. Of course the steak was no longer medium-rare and my fish was pretty awful. The most annoying thing is that he/manager NEVER acknowledged my meal being cold and removing it from the bill. Only my son's steak. Why? I don't know. In general, I think the food here is overpriced and very underwhelming. Now I know and I don't need to go back.Food did not have the flavors outlined in the descriptions. Our Waitress was very good though (not her fault the food was not to par for the price). The bread and whipped butter was excellent

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    Trail Break - tacos - Updated August 2026

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