All Star Sandwich Bar
1245 Cambridge st.
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.
89 Winthrop Street
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.
907 Boylston St.
Boston MA 02115
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.
150 Highland Avenue
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.