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Find Business Insurance Agents Near You in Pittsfield, MA

Browse business insurance agents serving Pittsfield, Massachusetts. Updated 2026-07-14.

The top-rated business insurance agent in Pittsfield, Massachusetts is Pearson Wallace Insurance, LLC, rated 4.9 stars across 113 reviews. Other highly rated options include AAA Pittsfield, Greylock Insurance Agency, MountainOne Insurance. This directory lists 20 business insurance agents serving Pittsfield.

Showing 20 business insurance agents in Pittsfield, MAListings are displayed in no particular order and are not ranked. Order does not constitute a recommendation or endorsement.

Comparison

Top 10 listings
#NameAddressPhone
1Pearson Wallace Insurance, LLC222 South St(413) 464-9390
2AAA Pittsfield660 Merrill Rd(413) 445-5635
3Greylock Insurance Agency5 Cheshire Rd Suite 26(413) 443-5943
4MountainOne Insurance111 Silver Lake Blvd(413) 442-9241
5Shire City Insurance446 South St #1(413) 443-9359
6Wheeler & Taylor Insurance402 East St(413) 448-8224
7Massachusetts Registered Agent LLC82 Wendell Ave STE 100(508) 475-6002
8Berkshire Insurance Group43 East St(866) 636-0244
9Taillefer Insurance446 South St(413) 445-5616
10Berkshire Fairfield Insurance Agency, LLC128 South St(413) 443-0077
PW
222 South St
Pearson Wallace Insurance, LLC
Business Insurance Agent · Pittsfield, MA

Pearson Wallace Insurance, LLC offers a range of business insurance services in Pittsfield, MA, including general liability, property coverage, and workers’ compensation. The agency provides ongoing policy reviews and claims support to help business owners maintain adequate protection as their operations evolve. Its account management plans include regular check-ins to adjust coverage for growing risks. Pearson Wallace services a variety of commercial properties, such as single-family homes, apartments, retail spaces, and restaurants.

AP
660 Merrill Rd
AAA Pittsfield
Business Insurance Agent · Pittsfield, MA

AAA Pittsfield serves the Pittsfield, Massachusetts metro area as a business insurance agent. The agency helps local companies manage commercial risks by offering customized coverage options. Its services include general liability and property insurance for small to mid-sized businesses. It also assists with workers’ compensation policies to protect employees and employers. Additional support is available through commercial auto insurance and business interruption coverage.

GI
5 Cheshire Rd Suite 26
Greylock Insurance Agency
Business Insurance Agent · Pittsfield, MA

Greylock Insurance Agency serves residential clients in Pittsfield, MA, helping to protect homes and personal assets with appropriate coverage. The agency also provides commercial insurance for local businesses, addressing liability, property, and other operational risks throughout Berkshire County. Agents work with clients to review changing needs, ensuring policies remain suitable over time. This ongoing relationship often leads to follow-up consultations and adjustments between regular service visits.

MI
111 Silver Lake Blvd
MountainOne Insurance
Business Insurance Agent · Pittsfield, MA

MountainOne Insurance is known for providing comprehensive business insurance solutions to companies in Pittsfield, MA. Its core services include general liability and property coverage, designed to protect local enterprises from common operational risks. The agency also offers workers' compensation policies to safeguard both employers and their staff. As a business insurance agent, it aims to match clients with appropriate commercial auto and cyber liability policies. Handling the unique exposures of contractors or retail shops remains a specialty service it can add on.

SC
446 South St #1
Shire City Insurance
Business Insurance Agent · Pittsfield, MA

Shire City Insurance in Pittsfield, MA distinguishes between one-off service needs and ongoing support for business coverage. As a business insurance agent, the firm helps select policies that protect commercial assets, liability exposure, and operational risks common in the local economy. Clients seeking occasional advice or single policy adjustments receive dedicated assistance. Meanwhile, businesses requiring continuous review and updated endorsements benefit from recurring consultations. Service runs on either a one-time, scheduled, or as-needed basis, depending on the client’s preference and how frequently their risk profile may change.

WT
402 East St
Wheeler & Taylor Insurance
Business Insurance Agent · Pittsfield, MA

Wheeler & Taylor Insurance in Pittsfield, MA provides specialty business insurance coverage, including liability, property, and workers’ compensation policies. It also offers standard commercial services tailored to local companies, helping them manage risk and secure the necessary protection for daily operations. The agency assists clients in that region with reviewing their policies before the winter season, ensuring adequate coverage for potential weather-related interruptions or property damage from snow and ice.

MR
82 Wendell Ave STE 100
Massachusetts Registered Agent LLC
Business Insurance Agent · Pittsfield, MA

As winter snow and ice threaten Berkshire County properties each year, Massachusetts Registered Agent LLC in Pittsfield helps local businesses secure their operations with commercial liability and property coverage. The agency guides entrepreneurs through the policy selection process, focusing on region-specific risks that affect enterprises of all sizes. Understanding that small business owners require clear explanations of often confusing insurance language, the team takes time to evaluate each client’s unique exposures and inventory. They begin every relationship by completing a thorough on-site inspection of the business premises.

BI
43 East St
Berkshire Insurance Group
Business Insurance Agent · Pittsfield, MA

Berkshire Insurance Group provides business insurance services to companies throughout Pittsfield, MA. Its agents assist with obtaining required liability policies and can arrange specialized add-ons for property protection or business interruption coverage. The firm works with clients to assess risk and secure appropriate policies for a range of commercial operations, including professional offices, industrial warehouses, and food service establishments.

TI
446 South St
Taillefer Insurance
Business Insurance Agent · Pittsfield, MA

Serving Pittsfield, Massachusetts, and the surrounding communities of Berkshire County, Taillefer Insurance provides business insurance agent services for local enterprises. It handles a range of commercial coverage needs, including general liability, property protection, and workers’ compensation policies to help companies manage operational risks. For a typical job, the agent begins by reviewing a client’s specific exposures and business size, then compares options from multiple carriers to tailor a suitable policy.

BF
128 South St
Berkshire Fairfield Insurance Agency, LLC
Business Insurance Agent · Pittsfield, MA

Berkshire Fairfield Insurance Agency, LLC in Pittsfield, Massachusetts distinguishes between one-time policy placements for immediate coverage needs and recurring service options for ongoing protection. Its primary focus as a business insurance agent is helping local companies secure coverage that safeguards assets and operations against common commercial risks, such as property damage or liability claims. These services operate on a scheduled basis, with regular policy reviews and renewals built into the agency’s recurring workflow for established clients.

GI
150 West St
Greylock Insurance Agency
Business Insurance Agent · Pittsfield, MA
(413) 236-4840
greylockinsurance.com
MI
101 South St
MountainOne Insurance
Business Insurance Agent · Pittsfield, MA
(413) 445-5648
mountainone.com/insurance
SF
128 South St
Scarafoni Financial Group LLC
Business Insurance Agent · Pittsfield, MA
(413) 443-5300
scarafonifinancial.com
NM
55 North St #304
Northwestern Mutual
Business Insurance Agent · Pittsfield, MA
(413) 499-0620
northwesternmutual.com/financial-professionals
NI
166 East St
Nationwide Insurance: Berkshire Insurance Group Inc.
Business Insurance Agent · Pittsfield, MA
(413) 447-7376
CS
111 Silver Lake Blvd
CPD&C/Stevenson & Co Insurance Agency
Business Insurance Agent · Pittsfield, MA
(413) 443-3581
BI
75 South Church Street Pittsfield Lenox
Berkshire Insurance Group
Business Insurance Agent · Pittsfield, MA
(866) 636-0244
DA
772 North St
Dwyer Agency-Eleanore Brown
Business Insurance Agent · Pittsfield, MA
(413) 442-3350
BI
Allendale Shopping Center, 39 Cheshire Rd
Berkshire Insurance Group Inc
Business Insurance Agent · Pittsfield, MA
(413) 447-3510
NY
7 North St Suite LL1
New York Life
Business Insurance Agent · Pittsfield, MA
(413) 442-8067
newyorklife.com

What Does a a Business Insurance Agent in Pittsfield Cost?

The cost of business insurance in Massachusetts varies by industry, revenue, and coverage limits. A small retail shop in Pittsfield might pay between $500 and $1,500 per year for general liability. A construction contractor could pay $2,000 to $5,000 annually for a package policy. Workers compensation rates are set by the state and depend on payroll and classification codes. This is general information and not insurance advice.

About business insurance agents in Pittsfield

Business insurance agents in Pittsfield, Massachusetts help local companies find coverage for liability, property, and workers compensation. Massachusetts law requires most employers to carry workers compensation insurance. Agents in the Berkshires can guide you through state-specific requirements and help you compare policies from multiple carriers.

Frequently Asked Questions

What types of business insurance do Pittsfield agents offer?

Agents in Pittsfield offer general liability, commercial property, workers compensation, and professional liability insurance. They can also help with commercial auto and business interruption policies tailored to your industry.

Is workers compensation insurance required in Massachusetts?

Yes, Massachusetts law requires almost all employers to carry workers compensation insurance. Failure to have coverage can result in fines and stop work orders. An agent can help you meet this legal requirement.

How can a Pittsfield agent help with Massachusetts specific risks?

A local agent understands risks common to the Berkshires region, such as weather-related property damage and seasonal tourism fluctuations. They can recommend coverage that addresses these local factors while complying with Massachusetts insurance regulations.

Business Insurance Agents in Other Massachusetts Cities

Listings are compiled from publicly available information. Inclusion does not constitute endorsement. Verify each business insurance agent's credentials and current standing with your state Department of Insurance.