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The highlands goal is to have classic homemade recipes. We also want your whole family to enjoy a meal together so we have kept our prices low for all these years. This isn't just another restaurant this is a community staple that has a legacy to preserve. Come enjoy everything from soups, salads, sandwhichs, seafood, salads and so much more.

Download our Menu!



100 Fenn St. Pittsfield MA.


Tuesday – Saturday
4pm to 9:30pm


Sunday 4pm-8:00pm


Closed Mondays

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Voted Best Chicken Wings at the Wing Fling!!!


Twisted Buffalo, Garlic Parm, Butter Rum, Buffalo or Terriyaki Wings Chicken Tenders 

Buffalo Chicken Tenders 

Side of Fries

Onion Rings 

Fried Mushrooms with

Horshradish Sauce 

Mozzerella Triangles 






Chicken Salad 


Turkey with Lettuce & Tomato  

Turkey & Bacon 

Bacon Lettuce & Tomato 

Lettuce Bacon & Mayonnaise 

Western or Eastern 


Tuna Fish Salad with Lettuce & Tomato 


Hot Dog 


Ham & Cheese 

Ham & Swiss 

Ham & Egg 

American or Swiss 

Filet of Fish 

Roast Beef Sandwhich 


Egg Salad Sandwich 

Fried Egg 

Salami & Egg 


Bacon & Egg 

Eggplant Parm 

Hot Eggplant Parm 


Hot Meatball Sandwhich 

Italian Sausage 

Hot Italian Sausage 

Veal Cutlet Sandwhich 

Hot Veal Cutlet Sandwhich 

Veal Parm Sandwhich 

Hot Veal Parm 

Chicken Cutlet Sandwhich 

Hot Chicken Parm 

Chicken Parm 

Grilled Chicken 

Grilled Cheese and Tuna 

Grilled American Cheese 

Grilled Cheese and Tomato 

Bacon Egg and Cheese Sand 




Large House Salad 

Side of Special Salad 

Highland Special Salad 

Side of Salad 


Grilled Chicken Salad 

or Crispy Chicken 

Grilled Chicken Ceaser Salad 

or Crispy Chicken 


Coffee or Tea



Hot Chocolate


Iced Tea or Iced Coffee


Lg Milk (pint)

Lg Juice (pint)


Italian Dishes


Highland Trio, Chicken Parm, 1 Sausage, 1 Meatball 

Eggplant Parm over Spaghetti 

Veal Scallopini, Spaghetti and Salad 

Veal Cutlet, Spaghetti and Salad 

Veal Parmigiana or Chicken Parmigiana, Spaghetti and Salad 

Chicken Parmesan, Spaghetti and Salad 

Southern Fried Chicken, Spaghetti and Salad 

Chicken Livers Saute, Spaghetti and Salad 

Italian Sausage and Peppers, Spaghetti and Salad 

Broiled Mushrooms, Spaghetti and Salad 

Large Order Spaghetti and Meatballs and Salad 

Large Order Spaghetti and Italian Sausage and Salad 

Small Order Spaghetti and One Meatball 

Small Order Spaghetti and No Meatball 

Small Order Spaghetti and Italian Sausage 

Side Order of Spaghetti and One Italian Sausage 

Side Order of Spaghetti and One Meatball 

Side Order of Spaghetti and No Meatball 



Roast Turkey, Mashed Potato, Stuffing, Veg and Cran Sauce 

Roast Beef, Mashed Potato and Veg 

Hot Turkey Sandwich, Mashed Potato and Cran Sauce 

Broiled Pork Tenderloin, Home Fried Pot, Applesauce 

Omelets, Western, Mushroom, Onion, Or Pepper, Mashed Pot & Veg 

Calves Liver, Mashed Potatos and Salad 

Hamburger Special, French Fries and Coleslaw 

Hamburger Pork Sausages, Mashed Pot, Applesauce 

Hamburger Steak with Onion Sauce, Mashed Potato and Veg 

Open Steak Sandwich on Toast, French Fries and Salad 

Sirloin Steak, French Fries, and Salad 

...with Mushroom Sauce 

Pork Chops, French Fries and Applesauce 





Fresh Shrimp Cocktail 

Fried Filet of Haddock, French Fries, Cole Slaw or Veg 

Fried Shrimp, French Fries, Cole Slaw or Veg 

Fried Scallops, French Fries, Cole Slaw or Veg 

Scallop Sandwich 








Ice Cream 

Ala Mode 



Changes to Spaghetti, Sliced Tomatos, Salad, Home Fries or French Fries $2 extra

Orders to go .50 extra   Sandwhiches to go  $.25


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