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    Tailwind Tavern

    3.8 (4 reviews)
    Closed 11:00 am - 11:00 pm
    Updated 3 months ago

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    Rail Trail Flatbread

    Rail Trail Flatbread

    4.3(184 reviews)
    2.5 mi
    $$
    Private events
    Kid friendly

    Enjoyed the Hudson location so was excited to stop here while nearby. Their menu is a good…read moreselection, everything seems to be made with fresh ingredients and they are known for their wood fired oven pizzas. We started with their truffle fries which were yummy. Four of us splitting them so one whipped feta cheese dip wasn't enough but we ordered another. My friend got the chicken parm which she really liked with the pesto pasta underneath. While a few of us split some pizzas. We got a large half and half of buffalo chicken and the primo pepperoni pizza. Then we wanted to try the sweet ricotta and vodka pizza special so we got a small. The special was so good!!!!!! Plus the other two are our favs so we knew they'd be good. Crust is yummy too. We also split the raspberry chocolate cake which was delicious. Our server Theo was also super helpful and took good care of us. Check out this place for a good dinner and support a local business!

    First off, Milford can be tricky to park in but Rail Trail has their own lot! I didn't know ahead…read moreof time and was pleasantly surprised. The inside of the restaurant definitely has a cool vibe and was a nice size. I do recommend making a reservation online in advance. At the end of the day I gave this spot a 3 only because the food was mediocre. I ordered a custom ricotta and pepperoni pizza and shared some fries. Both left me feeling disappointed (and I am not a picky pizza person, trust me).

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    Rail Trail Flatbread
    Rail Trail Flatbread
    Rail Trail Flatbread

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    CraftRoots Brewing - Live Music

    CraftRoots Brewing

    4.4(61 reviews)
    2.7 mi
    $$

    CraftRoots in Milford is exactly what I love about living in the metrowest community. Not only are…read morethey pumping out tasty craft beer, they're also giving it all back to the community. CraftRoots is a 501(c)3 non-profit and each month they select a new local charity to support. How amazing is that?! AND the best part?! It really is GREAT craft beer and even greater people. The flight is the perfect way to mix and match to find your go to pint for the evening. The staff are funny, engaging, and super kind, and the owners are some of the most down to earth, kind hearted folks I've met. PS - the live music was AMAZING and they have board games you can play too! If you get hungry there's always a local food truck standing by! My recommendations? Ms. American Pie (with sugar rim!) and the Ode to The Cranberries!

    Fun place, small brewery with decent offerings on tap. Typically I go on a weekend night (Fri or…read moreSat) they generally have live music. There brews range from a lite lager, to NE style IPA's to a stout, something for all tastes. For food it varries, they do have snacks but the real food comes from food trucks so check the website to see who's serving it up on the day you're going, the taco truck seems to be a crowd favorite but it can vary. The setting is industrial garage, I like the look of the stainless steel vats that ferment the brews. The people who operate the place are very friendly and welcoming, the crowd can range from early 20 somethings to 60 somethings, dancing is encouraged. If you're a beer afficianado stop in for pint and make a new friend.

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    CraftRoots Brewing - Interior

    Interior

    CraftRoots Brewing - Mug Club and beers to go

    Mug Club and beers to go

    CraftRoots Brewing - Newly renovated space

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    Newly renovated space

    Tailwind Tavern - salad - Updated May 2026

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