Jobs in Chestertown, MD
30 active postings tracked in Chestertown, MD · collapsed to 28 roles.
65
/ 100
Stable
Chestertown, MD Job Market Score
Driven by
- Net hiring is positive (+11 this week — 11 added vs 0 removed)
- Few reposted listings (7% appear duplicated)
- Most postings refresh within a month (30% open 30+ days)
Chestertown, MD job market overview (May 2026)
The Chestertown, MD job market is currently stable, with a mix of fresh hiring and slower-moving roles. Out of 30 active job postings tracked here, 30% have been open for more than 30 days. Hiring is concentrated in store supervisor / manager and retail associate, with retail as the leading sector.
- 30% of postings in Chestertown, MD have been open for more than 30 days, which may indicate slower hiring or reposted positions.
- 11 new postings have appeared this week — about 37% of currently-active listings.
- Half of active postings here have been open 17 days or fewer. The longest 10% have been open for 3546+ days.
- 3% of postings list a salary range (1 of 30).
- The most active employers right now are Walgreens, Dollar General, and KFC.
What this means for job seekers
- Expect a typical mix of fast and slow-moving roles.
- Best opportunities are in store supervisor / manager and retail associate.
- Many employers don't list salary — be ready to ask early.
Chestertown, MD job market
Aggregated from currently-active postings tracked in Chestertown, MD.
- 30Active postings
- 11Posted this week
- 9Open 30+ days30% of active
- 0Remote / hybrid0% of active
- 3%List salary1 of 30
- 0%Hourly0 of disclosed
- —Median annual (max)
- —Median hourly (max)
- 17dMedian agep90 3546d (long tail)
Top categories
- Store Supervisor / Manager6
- Retail Associate3
- Pharmacy2
- Shift Supervisor / Service Lead2
- Restaurant Manager / GM2
- Customer Success1
Top occupations (SOC)
- First-Line Supervisors of Food Preparation and Serving Workers2
- Fast Food and Counter Workers2
- Retail Salespersons2
- General and Operations Managers1
- Customer Service Representatives1
Top sectors
- Retail22
- Healthcare9
- Food Service / Restaurants8
- Financial Services1
- Telecommunications1
Employment mix
- Unspecified24 · 80%
- Intern2 · 7%
- Temporary2 · 7%
- Part-time1 · 3%
- Contract1 · 3%
Top hiring companies
Filter by skill
Recent postings
- Pharmacy Technician / Pharm Tech ApprenticeshipPharmacy
Walgreens · Chestertown, Maryland · jobs.walgreens.com
posted 4 days ago
- Team MemberCrew / Cashier
Tractor Supply · Chestertown, Maryland · tractorsupply.careers
posted 2 weeks ago
- Merchandising Sales Associate
Tractor Supply · Chestertown, Maryland · tractorsupply.careers
posted 2 weeks ago