| $150,000–350,000 | RAY'S AUTOMOTIVE INC | WATERBURY, CT | Berkshire Bank |
| $350,000–1 million | RAYBEN ENTERPRISES, INC. | ALBANY, NY | Berkshire Bank |
| $150,000–350,000 | RED BIRD FITNESS, LLC | SPRINGFIELD, MA | Berkshire Bank |
| $150,000–350,000 | REGGIES INC | BLACKWOOD, NJ | Berkshire Bank |
| $150,000–350,000 | REID SOUND, INC. | WINDSOR, NJ | Berkshire Bank |
| $350,000–1 million | REIMEL MACHINE, INC. | WILLOW GROVE, PA | Berkshire Bank |
| $350,000–1 million | RELOTRANS LIMITED PARTNERSHIP | NEWBURYPORT, MA | Berkshire Bank |
| $1–2 million | RENBROOK SCHOOL INC | WEST HARTFORD, CT | Berkshire Bank |
| $150,000–350,000 | RESEARCH PACKAGING INC | AVON, MA | Berkshire Bank |
| $350,000–1 million | RESTECH PLASTIC MOLDING, LLC | HUDSON, MA | Berkshire Bank |
| $350,000–1 million | RESTOREPRO CONTRACTING INC | HIGHTSTOWN, NJ | Berkshire Bank |
| $150,000–350,000 | RESTOREPRO CONTRACTING LLC | HIGHTSTOWN, NJ | Berkshire Bank |
| $350,000–1 million | REVOLUTIONARY SPACES, INC. | BOSTON, MA | Berkshire Bank |
| $150,000–350,000 | RFB ASSOCIATES INC | SCHENECTADY, NY | Berkshire Bank |
| $350,000–1 million | RICASOLI & SANTIN CONTRACTING CO INC | TRENTON, NJ | Berkshire Bank |
| $350,000–1 million | RICHARD OBREZA TRUCKING, INC. | MOHAWK, NY | Berkshire Bank |
| $1–2 million | RITTER CONTRACTING INC | CHURCHVILLE, PA | Berkshire Bank |
| $150,000–350,000 | ROBATEL INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ROBERT GUEN, DMD & ASSOCIATES, LLC | BROOKLINE, MA | Berkshire Bank |
| $350,000–1 million | ROBERTS ENERGY, LLC | SPRINGFIELD, MA | Berkshire Bank |
| $350,000–1 million | ROCKERBOX INC | NEW YORK, NY | Berkshire Bank |
| $150,000–350,000 | ROCKY HILL PEDIATRICS LLC | ROCKY HILL, CT | Berkshire Bank |
| $350,000–1 million | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE | SPRINGFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR BLESSED SACRAMENT PARISH | HOLYOKE, MA | Berkshire Bank |
| $150,000–350,000 | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST AGNES PARISH | DALTON, MA | Berkshire Bank |
| $150,000–350,000 | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST JOHN THE BAPTIST SCHOOL | LUDLOW, MA | Berkshire Bank |
| $350,000–1 million | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST MARY PARISH | WESTFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST MARY PARISH | LONGMEADOW, MA | Berkshire Bank |
| $350,000–1 million | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST MICHAEL'S ACADEMY | SPRINGFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST STANISLAUS SCHOOL | CHICOPEE, MA | Berkshire Bank |
| $150,000–350,000 | ROMAN CATHOLIC BISHOP OF SPRINGFIELD A CORP SOLE FOR ST THOMAS THE APOSTLE PARIS | WEST SPRINGFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ROME HOSPITALITY GROUP, LLC | ROME, NY | Berkshire Bank |
| $150,000–350,000 | RONNIE'S CYCLE SALES OF BENNINGTON, INC | BENNINGTON, VT | Berkshire Bank |
| $150,000–350,000 | RONNIE'S CYCLE SALES OF PITTSFIELD, INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | ROSEN & ASSOCIATES, LLP | WESTBOROUGH, MA | Berkshire Bank |
| $150,000–350,000 | ROYAL FOOD IMPORT CORPORATION | BOSTON, MA | Berkshire Bank |
| $150,000–350,000 | RPCG, LLC | GLASTONBURY, CT | Berkshire Bank |
| $150,000–350,000 | RPM INDUSTRIES, INC. | PORTLAND, CT | Berkshire Bank |
| $350,000–1 million | RSTZ TRANSPORT, INC. | WEBSTER, MA | Berkshire Bank |
| $150,000–350,000 | RUTLAND NURSERIES INC | RUTLAND, MA | Berkshire Bank |
| $150,000–350,000 | RUTLANDS TURF PRO | RUTLAND, MA | Berkshire Bank |
| $150,000–350,000 | RV HEALTHCARE ANALYTICS LLC | NEW YORK, NY | Berkshire Bank |
| $2–5 million | S & S STAFFING, LLC | WORCESTER, MA | Berkshire Bank |
| $150,000–350,000 | S.S.R. CORPORATION | NEWPORT, RI | Berkshire Bank |
| $350,000–1 million | SACCUCCI AUTO GROUP, INC. | MIDDLETOWN, RI | Berkshire Bank |
| $150,000–350,000 | SADAT ASSOCIATES, INC | TRENTON, NJ | Berkshire Bank |
| $350,000–1 million | SAINT ANN'S CHURCH | LAWRENCE TOWNSHIP, NJ | Berkshire Bank |
| $150,000–350,000 | SALITSKY ALLOYS INC | HOLDEN, MA | Berkshire Bank |
| $150,000–350,000 | SALON DESIGNS, INC. | FRAMINGHAM, MA | Berkshire Bank |
| $150,000–350,000 | SAM'S FUN CITY INC. | PENSACOLA, FL | Berkshire Bank |
| $350,000–1 million | SAMPCO INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SAMPCO OF INDIANA INC | SOUTH BEND, IN | Berkshire Bank |
| $350,000–1 million | SAMPCO OF PENNSYLVANIA INC | CHESWICK, PA | Berkshire Bank |
| $150,000–350,000 | SAMPCO OF TEXAS INC | CEDAR HILL, TX | Berkshire Bank |
| $150,000–350,000 | SAND CASTLES LEARNING CENTER INC. | RUTHERFORD, NJ | Berkshire Bank |
| $150,000–350,000 | SATCH SALES, INC | ALBANY, NY | Berkshire Bank |
| $150,000–350,000 | SAUL FUNERAL HOMES INC | HAMILTON SQUARE, NJ | Berkshire Bank |
| $350,000–1 million | SCHOOL BASED SERVICES, INC | HOLYOKE, MA | Berkshire Bank |
| $350,000–1 million | SCHUIBBEO HOLDINGS INC. | MECHANICSBURG, PA | Berkshire Bank |
| $350,000–1 million | SCOTT ELECTROKRAFTS, INC | ANDOVER, CT | Berkshire Bank |
| $1–2 million | SEGUE MANUFACTURING SERVICES LLC | NORTH BILLERICA, MA | Berkshire Bank |
| $150,000–350,000 | SEMNOX SOLUTIONS LLC | DALLAS, TX | Berkshire Bank |
| $150,000–350,000 | SENIOR CARE OF PRINCETON LLC | PRINCETON JUNCTION, NJ | Berkshire Bank |
| $150,000–350,000 | SERAJ WIRELESS, LLC | ALBANY, NY | Berkshire Bank |
| $150,000–350,000 | SH LAW SOLUTIONS PC | DENVER, CO | Berkshire Bank |
| $350,000–1 million | SHACK FOOD OF CONNECTICUT LLC | BOSTON, MA | Berkshire Bank |
| $350,000–1 million | SHACK FOODS OF BACK BAY LLC | BOSTON, MA | Berkshire Bank |
| $150,000–350,000 | SHAMROCK ELECTRIC INC. | MIDDLETOWN, RI | Berkshire Bank |
| $350,000–1 million | SHARBELL BUILDING COMPANY LLC | ROBBINSVILLE, NJ | Berkshire Bank |
| $150,000–350,000 | SHEA'S ELECTRICAL INC. | TOLLAND, CT | Berkshire Bank |
| $350,000–1 million | SHEEHAN HEALTH GROUP, LLC | SOUTHBOROUGH, MA | Berkshire Bank |
| $150,000–350,000 | SHEFFIELD POTTERY, INC. | SHEFFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SHENKER RUSSO & CLARK LLP | ALBANY, NY | Berkshire Bank |
| $150,000–350,000 | SHORELINE STONE LLC | PAWCATUCK, CT | Berkshire Bank |
| $1–2 million | SHREWSBURY NURSING & REHABILITATION CENTER, INC. | SHREWSBURY, MA | Berkshire Bank |
| $350,000–1 million | SIGNATURE SAFETY LLC | BRICK, NJ | Berkshire Bank |
| $150,000–350,000 | SINGH FAMILY VENTURES LLC | HAMILTON, NJ | Berkshire Bank |
| $350,000–1 million | SLP CAPITAL LLC | WOODBRIDGE, CT | Berkshire Bank |
| $150,000–350,000 | SOLARFLAIR ENERGY, INC | ASHLAND, MA | Berkshire Bank |
| $1–2 million | SOLDIER ON INC | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SOLDIER ON OF DELAWARE INC. | PITTSFIELD, MA | Berkshire Bank |
| $150,000–350,000 | SOREL'S GARAGE INC. | BROOKLYN, CT | Berkshire Bank |
| $150,000–350,000 | SOUTH STREAM SEAFOODS, INC. | WARWICK, RI | Berkshire Bank |
| $2–5 million | SOUTHEAST MA SNF LLC | NORTH EASTON, MA | Berkshire Bank |
| $150,000–350,000 | SOUTHEASTERN CONNECTICUT ENTERPRISE REGION CORP | GROTON, CT | Berkshire Bank |
| $350,000–1 million | SOUTHSHORE MA SNF LLC | ROCKLAND, MA | Berkshire Bank |
| $350,000–1 million | SPACE AGE ELECTRONICS INC | STERLING, MA | Berkshire Bank |
| $1–2 million | SPAULDING COMPOSITES, INC. | ROCHESTER, NH | Berkshire Bank |
| $150,000–350,000 | SPEAKEASY STAGE CO. INC | BOSTON, MA | Berkshire Bank |
| $350,000–1 million | SPECIALTY FOODS BOSTON, INC | BOSTON, MA | Berkshire Bank |
| $350,000–1 million | SPRINGDALE EDUCATION CENTER, INC. | HOLYOKE, MA | Berkshire Bank |
| $150,000–350,000 | SPRINGFIELD BOYS & GIRLS CLUB, INC. | SPRINGFIELD, MA | Berkshire Bank |
| $150,000–350,000 | ST JAMES CATHOLIC CHURCH | DANIELSON, CT | Berkshire Bank |
| $150,000–350,000 | ST. CLEMENTS, INC. | PORTLAND, CT | Berkshire Bank |
| $150,000–350,000 | STADIUM HOLDINGS, INC | LENEXA, KS | Berkshire Bank |
| $350,000–1 million | STANLEY LAW OFFICES LLP | SYRACUSE, NY | Berkshire Bank |
| $350,000–1 million | STARBASE TECHNOLOGIES INC. | PITTSFIELD, MA | Berkshire Bank |
| $350,000–1 million | STARFIELD & SMITH, P.C. | FORT WASHINGTON, PA | Berkshire Bank |
| $150,000–350,000 | STEPHENS CHRYSLER JEEP DODGE OF GREENWICH LLC | GREENWICH, NY | Berkshire Bank |
| $150,000–350,000 | STEPHENS OF BENNINGTON | BENNINGTON, VT | Berkshire Bank |