Due to marked reductions in morbidity and mortality, antiretroviral (ARV) adherence monitoring is of high interest. Researchers and clinicians often resort to the most feasible and cost-effective adherence methods possible, which may result in biased or inaccurate estimates and require the physical presence of a participant at a research or clinic site. The objective of our study was to evaluate the feasibility and acceptability of three objective, innovative, and remote methods to estimate ARV adherence which may be conducted with less time and financial resources in a wide range of clinic and research settings. These three methods included: (a) text-messaged photographs of pharmacy refill dates to measure refill-based adherence, (b) text-messaged photographs of ARV medications to estimate pill-count-based adherence, and (c) home-collected hair samples for the measurement of ARV concentration to determine pharmacologic-based adherence. We conducted a pilot study from March through October 2017 to examine the feasibility and acceptability of these three adherence measures and the remotely conducted study procedures in 93 adults living with HIV nationwide. From our diverse national sample of participants, 95.7% were retained until the end of the study, 89.9% sent all text messages, and 84.3% sent all hair samples. Approximately 74.2% of participants reported excellent overall experience with the study, 60.2% were very or extremely satisfied with participating in a hair collection study, and 76.3% noted extremely high likelihood of participating in a similar study including text messaging pictures of medications or refill dates. We noted high levels of feasibility and acceptability with the remote study methodology, collection of photographed and text messaged pharmacy refill dates and pill counts, and home-collected hair samples. Here we describe the feasibility and acceptability metrics, results from the exit qualitative interviews with the participants, and lessons learned. These adherence measures represent innovative approaches to expand monitoring tools for HIV treatment and prevention adherence in future research.