Boston's Best Chili
All Star Sandwich Bar
1245 Cambridge st.
Cambridge, MA
(617) 868-3065
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All Star's spicy Texas State Penn Chili is heavy on the shredded beef brisket and served up with sour cream, onions, jack cheese, lime and a side of cornbread. If you know anything about Texas-style chili, there is no room any 'filler.' So if you like your chili with beans, stay away.
Grendel's Den
89 Winthrop Street
Cambridge, MA
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While equally delicious, you may be able to guess that Grendel's Homemade Vegan Chili is the complete opposite end of the spectrum as All Star's. A hearty five-bean chili with tortilla chips topped with a spoonful of cilantro pesto.
Pour House
907 Boylston St.
Boston MA 02115
(617) 236-1767
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This popular Boylston Street dive bar serves up a spicy homemade Fire House Chili that is loaded up with melted cheddar cheese and served with tortilla chips. How spicy is it? Stealing a joke from the Pour House website, "Good thing the fire department is only six doors down." On a serious note, if you need something to wash down the chili with, the beer at Pour House is cheap.
Highland Kitchen
150 Highland Avenue
Somerville, MA
(617) 625-1131
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Highland's chili is more than just an eating experience. Their Spicy Texas Style Beef Chili pairs well with their Mark and Stormy. The homemade drink is a mix of Maker's Mark and spicy homemade chili infused ginger beer. It's a fantastic balance of sweet and spicy.